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CAS 3886-69-9
(R)-1-phenylethan-1-amine(R)-(-)-1-Phenylethylamine
Codes: ATOR-012, Tamsulosin Hydrochloride-002, ROSU-039, FINA-034, SITAF-010, MITI-013
Application context (from source-drug indications)
Type 2 diabetesAtorvastatin Calcium Hydrate/Metformin HydrochlorideHyperlipidaemiaAtorvastatin Calcium Hydrate/Metformin HydrochlorideErectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinHypertensionFimasartan potassium trihydrate/Rosuvastatin calciumDyslipidaemiaFimasartan potassium trihydrate/Rosuvastatin calciumHypertensionRosuvastatin Calcium/TelmisartanHyperlipidaemiaRosuvastatin Calcium/TelmisartanOtitis externaFinafloxacinOtitis media with effusionFinafloxacinOtitis mediaFinafloxacinUrinary tract infectionFinafloxacinPyelonephritisFinafloxacinGram-negative bacterial infectionFinafloxacinHypertensionAtorvastatin Calcium Hydrate/IrbesartanHyperlipidaemiaAtorvastatin Calcium Hydrate/IrbesartanLower urinary tract symptomsSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaSolifenacin Succinate/Tamsulosin HydrochlorideOveractive bladderSolifenacin Succinate/Tamsulosin HydrochlorideDrug-related adverse effects and reactionsSolifenacin Succinate/Tamsulosin HydrochlorideBladder neck obstructionSolifenacin Succinate/Tamsulosin HydrochlorideBenign prostatic hyperplasiaDutasteride/Tamsulosin HydrochlorideHypercholesterolaemiaAtorvastatin Calcium Hydrate/RamiprilHypertensionAtorvastatin Calcium Hydrate/RamiprilCystitisSitafloxacin HydrateSinusitisSitafloxacin HydrateTonsillitisSitafloxacin HydratePneumoniaSitafloxacin HydrateCervicitisSitafloxacin HydratePericoronitisSitafloxacin HydrateHyperlipoproteinaemia type IIIAtorvastatin Calcium HydrateHyperlipidaemiaAtorvastatin Calcium HydrateHeterozygous familial hypercholesterolaemiaAtorvastatin Calcium HydrateHeart failureAtorvastatin Calcium HydrateType 2 diabetesAtorvastatin Calcium HydrateStrokeAtorvastatin Calcium HydrateBenign prostatic hyperplasiaTamsulosin HydrochlorideUrinary tract infectionTamsulosin HydrochlorideUrinary retentionTamsulosin HydrochlorideInguinal herniaTamsulosin HydrochlorideVoiding dysfunctionTamsulosin HydrochlorideLower urinary tract symptomsTamsulosin HydrochlorideHomozygous familial hypercholesterolaemiaRosuvastatin CalciumHeterozygous familial hypercholesterolaemiaRosuvastatin CalciumHyperlipoproteinaemia type IIIRosuvastatin CalciumAtherosclerosisRosuvastatin CalciumHyperlipoproteinaemia type IIRosuvastatin CalciumHypercholesterolaemiaRosuvastatin CalciumType 2 diabetesMitiglinideDiabetesMitiglinide
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Atorvastatin Calcium Hydrate/Metformin Hydrochloride | Tier C — Watch / trade | - |
| Tadalafil/Tamsulosin | Tier C — Watch / trade | - |
| Fimasartan potassium trihydrate/Rosuvastatin calcium | Tier C — Watch / trade | - |
| Rosuvastatin Calcium/Telmisartan | Tier C — Watch / trade | - |
| Finafloxacin | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate/Irbesartan | Tier C — Watch / trade | - |
| Solifenacin Succinate/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Dutasteride/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate/Ramipril | Tier C — Watch / trade | - |
| Sitafloxacin Hydrate | Tier C — Watch / trade | - |
| Atorvastatin Calcium Hydrate | Tier B — Position early | - |
| Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Rosuvastatin Calcium | Tier B — Position early | - |
| Mitiglinide | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
ethyl 2-bromo-2-(4-fluorophenyl)acetate→2-(1,3-dioxolan-2-yl)ethanamine→ethyl 2-((2-(1,3-dioxolan-2-yl)ethyl)amino)-2-(4-fluorophenyl)acetate→isobutyryl chloride→2-(N-(2-(1,3-dioxolan-2-yl)ethyl)isobutyramido)-2-(4-fluorophenyl)acetic acid→N,3-diphenylpropiolamide→1-(2-(1,3-dioxolan-2-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide→methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-5-hydroxy-3-oxoheptanoate→(3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→(R)-1-phenylethan-1-amine→1-((3R,5R)-3,5-dihydroxy-7-oxo-7-(((R)-1-phenylethyl)amino)heptyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2R)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-amine hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→(2-Ethoxyphenoxy)acetaldehyde→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-(2-Bromoethoxy)-2-ethoxybenzene→1-Hydroxy-2-ethoxybenzene→1,3-Dioxolan-2-one→2-(2-Ethoxyphenoxy)ethanol
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→5-[(2R)-2-aminopropyl]-2-methoxybenzene-1-sulfonic acid→1-(2-Bromoethoxy)-2-ethoxybenzene→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonic acid→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonyl chloride
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2E)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-imine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→(+/-)-tert-Butyl sulfinamide→(SR)-N-[(2E)-1-(4-Methoxyphenyl)propan-2-ylidene]-2-methylpropane-2-sulfinamide→(SR)-N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→Chloridosulfuric acid→2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonyl chloride→1,1-Dimethylethylamine→N-tert-Butyl-2-methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→N-tert-Butyl-2-methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-Aminopropyl]-N-tert-butyl-2-methoxybenzene-1-sulfonamide→(2-Ethoxyphenoxy)acetonitrile→1-Hydroxy-2-ethoxybenzene→2-Chloroacetonitrile→N-tert-Butyl-5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-1-sulfonamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl carbonochloridate→methyltriphenylphosphonium bromide→4-((tert-butyldimethylsilyl)oxy)dihydro-2H-pyran-2,6(3H)-dione→(R)-1-phenylethan-1-amine→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic acid→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic (methyl carbonic) anhydride→(R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-N-((R)-1-phenylethyl)-6-(triphenyl-l5-phosphanylidene)hexanamide→(R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxy-N-((R)-1-phenylethyl)hept-6-enamide
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl carbonochloridate→methyltriphenylphosphonium bromide→4-((tert-butyldimethylsilyl)oxy)dihydro-2H-pyran-2,6(3H)-dione→(R)-1-phenylethan-1-amine→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic acid→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic (methyl carbonic) anhydride→(R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-N-((R)-1-phenylethyl)-6-(triphenyl-l5-phosphanylidene)hexanamide→(R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxy-N-((R)-1-phenylethyl)hept-6-enamide
2,4-dichloro-3-cyano-5-fluorobenzoyl chloride→(Z)-ethyl 3-(dimethylamino)acrylate→ethyl 2-(2,4-dichloro-3-cyano-5-fluorobenzoyl)-3-(dimethylamino)acrylate→cyclopropanamine→ethyl 3-(cyclopropylamino)-2-(2,4-dichloro-3-cyano-5-fluorobenzoyl)acrylate→ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate→(E)-but-2-ene-1,4-diol→1-tosyl-2,5-dihydro-1H-pyrrole→3-tosyl-6-oxa-3-azabicyclo[3.1.0]hexane→2,4-dichloro-1-fluorobenzene→1-(2,4-dichloro-5-fluorophenyl)ethanone→2,4-dichloro-5-fluorobenzoic acid→2,4-dichloro-5-fluoro-3-nitrobenzoic acid→methyl 2,4-dichloro-5-fluoro-3-nitrobenzoate→methyl 3-amino-2,4-dichloro-5-fluorobenzoate→methyl 2,4-dichloro-3-cyano-5-fluorobenzoate→2,4-dichloro-3-cyano-5-fluorobenzoic acid→(4aS,7aS)-tert-butyl hexahydropyrrolo[3,4-b][1,4]oxazine-4(4aH)-carboxylate→(4aS,7aS)-tert-butyl 6-(8-cyano-1-cyclopropyl-3-(ethoxycarbonyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)hexahydropyrrolo[3,4-b][1,4]oxazine-4(4aH)-carboxylate→7-((4aS,7aS)-4-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-b][1,4]oxazin-6(2H)-yl)-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid→(E)-1,4-dichlorobut-2-ene→(R)-1-phenylethan-1-amine→(3S,4S)-4-(((R)-1-phenylethyl)amino)-1-tosylpyrrolidin-3-ol→2-chloroacetyl chloride→2-chloro-N-((3S,4S)-4-hydroxy-1-tosylpyrrolidin-3-yl)-N-((R)-1-phenylethyl)acetamide→(4aS,7aS)-4-((R)-1-phenylethyl)-6-tosylhexahydropyrrolo[3,4-b][1,4]oxazin-3(2H)-one→(4aS,7aS)-4-((R)-1-phenylethyl)-6-tosyloctahydropyrrolo[3,4-b][1,4]oxazine→(4aS,7aS)-6-tosyloctahydropyrrolo[3,4-b][1,4]oxazine→(4aS,7aS)-tert-butyl 6-tosylhexahydropyrrolo[3,4-b][1,4]oxazine-4(4aH)-carboxylate
ethyl 2-bromo-2-(4-fluorophenyl)acetate→2-(1,3-dioxolan-2-yl)ethanamine→ethyl 2-((2-(1,3-dioxolan-2-yl)ethyl)amino)-2-(4-fluorophenyl)acetate→isobutyryl chloride→2-(N-(2-(1,3-dioxolan-2-yl)ethyl)isobutyramido)-2-(4-fluorophenyl)acetic acid→N,3-diphenylpropiolamide→1-(2-(1,3-dioxolan-2-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide→methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-5-hydroxy-3-oxoheptanoate→(3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→(R)-1-phenylethan-1-amine→1-((3R,5R)-3,5-dihydroxy-7-oxo-7-(((R)-1-phenylethyl)amino)heptyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 9total yield: 50.8g(Tamsulosin (Free))
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2R)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-amine hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→(2-Ethoxyphenoxy)acetaldehyde→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-(2-Bromoethoxy)-2-ethoxybenzene→1-Hydroxy-2-ethoxybenzene→1,3-Dioxolan-2-one→2-(2-Ethoxyphenoxy)ethanol
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→5-[(2R)-2-aminopropyl]-2-methoxybenzene-1-sulfonic acid→1-(2-Bromoethoxy)-2-ethoxybenzene→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonic acid→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonyl chloride
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 5total yield: 46.28gTamsulosin Hydrochloride (API)
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2E)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-imine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→(+/-)-tert-Butyl sulfinamide→(SR)-N-[(2E)-1-(4-Methoxyphenyl)propan-2-ylidene]-2-methylpropane-2-sulfinamide→(SR)-N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→Chloridosulfuric acid→2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonyl chloride→1,1-Dimethylethylamine→N-tert-Butyl-2-methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→N-tert-Butyl-2-methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-Aminopropyl]-N-tert-butyl-2-methoxybenzene-1-sulfonamide→(2-Ethoxyphenoxy)acetonitrile→1-Hydroxy-2-ethoxybenzene→2-Chloroacetonitrile→N-tert-Butyl-5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-1-sulfonamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2R)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-amine hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→(2-Ethoxyphenoxy)acetaldehyde→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-(2-Bromoethoxy)-2-ethoxybenzene→1-Hydroxy-2-ethoxybenzene→1,3-Dioxolan-2-one→2-(2-Ethoxyphenoxy)ethanol
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→5-[(2R)-2-aminopropyl]-2-methoxybenzene-1-sulfonic acid→1-(2-Bromoethoxy)-2-ethoxybenzene→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonic acid→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonyl chloride
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 5total yield: 46.28gTamsulosin Hydrochloride (API)
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2E)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-imine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→(+/-)-tert-Butyl sulfinamide→(SR)-N-[(2E)-1-(4-Methoxyphenyl)propan-2-ylidene]-2-methylpropane-2-sulfinamide→(SR)-N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→Chloridosulfuric acid→2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonyl chloride→1,1-Dimethylethylamine→N-tert-Butyl-2-methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→N-tert-Butyl-2-methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-Aminopropyl]-N-tert-butyl-2-methoxybenzene-1-sulfonamide→(2-Ethoxyphenoxy)acetonitrile→1-Hydroxy-2-ethoxybenzene→2-Chloroacetonitrile→N-tert-Butyl-5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-1-sulfonamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
ethyl 2-bromo-2-(4-fluorophenyl)acetate→2-(1,3-dioxolan-2-yl)ethanamine→ethyl 2-((2-(1,3-dioxolan-2-yl)ethyl)amino)-2-(4-fluorophenyl)acetate→isobutyryl chloride→2-(N-(2-(1,3-dioxolan-2-yl)ethyl)isobutyramido)-2-(4-fluorophenyl)acetic acid→N,3-diphenylpropiolamide→1-(2-(1,3-dioxolan-2-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide→methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-5-hydroxy-3-oxoheptanoate→(3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→(R)-1-phenylethan-1-amine→1-((3R,5R)-3,5-dihydroxy-7-oxo-7-(((R)-1-phenylethyl)amino)heptyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate→(Z)-ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)-3-ethoxyacrylate→tert-butyl ((1R,2S)-2-fluorocyclopropyl)carbamate→ethyl (Z)-2-(3-chloro-2,4,5-trifluorobenzoyl)-3-(((1R,2S)-2-fluorocyclopropyl)amino)acrylate→ethyl 8-chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate→8-chloro-6,7-difluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid→SITAF-007→7-((S)-7-((tert-butoxycarbonyl)amino)-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1R,2S)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid→2-fluorocyclopropane-1-carboxylic acid→(R)-1-phenylethan-1-amine→2-fluoro-N-((R)-1-phenylethyl)cyclopropane-1-carboxamide→2-fluoro-N-((R)-1-phenylethyl)cyclopropane-1-carboxamide→(1S,2S)-2-fluoro-N-((R)-1-phenylethyl)cyclopropane-1-carboxamide→ethyl 3-oxobutanoate→1,2-dibromoethane→ethyl 1-acetylcyclopropane-1-carboxylate→ethyl 1-(2-bromoacetyl)cyclopropane-1-carboxylate→(R)-5-(1-phenylethyl)-5-azaspiro[2.4]heptane-4,7-dione→(R,Z)-7-(hydroxyimino)-5-(1-phenylethyl)-5-azaspiro[2.4]heptan-4-one→(S)-7-amino-5-((R)-1-phenylethyl)-5-azaspiro[2.4]heptan-4-one→(S)-5-((R)-1-phenylethyl)-5-azaspiro[2.4]heptan-7-amine→tert-butyl ((S)-5-((R)-1-phenylethyl)-5-azaspiro[2.4]heptan-7-yl)carbamate
ethyl 2-bromo-2-(4-fluorophenyl)acetate→2-(1,3-dioxolan-2-yl)ethanamine→ethyl 2-((2-(1,3-dioxolan-2-yl)ethyl)amino)-2-(4-fluorophenyl)acetate→isobutyryl chloride→2-(N-(2-(1,3-dioxolan-2-yl)ethyl)isobutyramido)-2-(4-fluorophenyl)acetic acid→N,3-diphenylpropiolamide→1-(2-(1,3-dioxolan-2-yl)ethyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-2-isopropyl-1-(3-oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide→methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-5-hydroxy-3-oxoheptanoate→(3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→(R)-1-phenylethan-1-amine→1-((3R,5R)-3,5-dihydroxy-7-oxo-7-(((R)-1-phenylethyl)amino)heptyl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide→sodium (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2R)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-amine hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→(2-Ethoxyphenoxy)acetaldehyde→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→1-(2-Bromoethoxy)-2-ethoxybenzene→1-Hydroxy-2-ethoxybenzene→1,3-Dioxolan-2-one→2-(2-Ethoxyphenoxy)ethanol
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→5-[(2R)-2-aminopropyl]-2-methoxybenzene-1-sulfonic acid→1-(2-Bromoethoxy)-2-ethoxybenzene→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzene-1-sulfonic acid→5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonyl chloride
2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→2-Methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzenesulfonamide hydrochloride→5-(2(R)-Aminopropyl)-2-methoxybenzenesulfonamide→5-[(2R)-2-Aminopropyl]-2-methoxybenzenesulfonamide hydrochloride→1-(2-Bromoethoxy)-2-ethoxybenzene→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide→2-(2-Ethoxyphenoxy)ethyl mesylate
1-(4-Methoxyphenyl)-2-propanone→(R)-(-)-1-Phenylethylamine→(2E)-1-(4-Methoxyphenyl)-N-[(1R)-1-phenylethyl]propan-2-imine→1-(4-Methoxyphenyl)-N-[1(R)-phenylethyl]propan-2(R)-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→(+/-)-tert-Butyl sulfinamide→(SR)-N-[(2E)-1-(4-Methoxyphenyl)propan-2-ylidene]-2-methylpropane-2-sulfinamide→(SR)-N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]-2-methylpropane-2-sulfinamide
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→Chloridosulfuric acid→2-Methoxy-5-(2-oxopropyl)benzene-1-sulfonyl chloride→1,1-Dimethylethylamine→N-tert-Butyl-2-methoxy-5-(2-oxopropyl)benzene-1-sulfonamide→(R)-(-)-1-Phenylethylamine→N-tert-Butyl-2-methoxy-5-[(2R)-2-[[(1R)-1-phenylethyl]amino]propyl]benzene-1-sulfonamide→5-[(2R)-2-Aminopropyl]-N-tert-butyl-2-methoxybenzene-1-sulfonamide→(2-Ethoxyphenoxy)acetonitrile→1-Hydroxy-2-ethoxybenzene→2-Chloroacetonitrile→N-tert-Butyl-5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzene-1-sulfonamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl carbonochloridate→methyltriphenylphosphonium bromide→4-((tert-butyldimethylsilyl)oxy)dihydro-2H-pyran-2,6(3H)-dione→(R)-1-phenylethan-1-amine→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic acid→(S)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-5-(((R)-1-phenylethyl)amino)pentanoic (methyl carbonic) anhydride→(R)-3-((tert-butyldimethylsilyl)oxy)-5-oxo-N-((R)-1-phenylethyl)-6-(triphenyl-l5-phosphanylidene)hexanamide→(R,E)-3-((tert-butyldimethylsilyl)oxy)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(R,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3-hydroxy-5-oxo-N-((R)-1-phenylethyl)hept-6-enamide→(3R,5S,E)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxy-N-((R)-1-phenylethyl)hept-6-enamide
diethyl succinate→(3aR,7aS)-octahydro-1H-isoindole→(S)-2-benzyl-4-((3aR,7aS)-octahydro-2H-isoindol-2-yl)-4-oxobutanoic acid→benzaldehyde→(Z)-3-(methoxycarbonyl)-4-phenylbut-3-enoic acid→(Z)-2-benzylidenesuccinic acid→(Z)-3-benzylidenedihydrofuran-2,5-dione→2-((Z)-benzylidene)-4-((3aR,7aS)-octahydro-2H-isoindol-2-yl)-4-oxobutanoic acid→(R)-1-phenylethan-1-amine
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