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CAS 58993-79-6
(-)-2-(4-Methoxyphenyl)-1-methylethanamine
Codes: Tamsulosin Hydrochloride-059
Application context (from source-drug indications)
Erectile dysfunctionTadalafil/TamsulosinBenign prostatic hyperplasiaTadalafil/TamsulosinLower 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 HydrochlorideBenign prostatic hyperplasiaTamsulosin HydrochlorideUrinary tract infectionTamsulosin HydrochlorideUrinary retentionTamsulosin HydrochlorideInguinal herniaTamsulosin HydrochlorideVoiding dysfunctionTamsulosin HydrochlorideLower urinary tract symptomsTamsulosin Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Tadalafil/Tamsulosin | Tier C — Watch / trade | - |
| Solifenacin Succinate/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Dutasteride/Tamsulosin Hydrochloride | Tier C — Watch / trade | - |
| Tamsulosin Hydrochloride | 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.
(-)-2-(4-Methoxyphenyl)-1-methylethanamine→2-Chloranylethanoyl chloride→2-chloro-N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]acetamide→5-[(2R)-2-(2-chloroacetamido)propyl]-2-methoxybenzene-1-sulfonyl chloride→2-chloro-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→1-Hydroxy-2-ethoxybenzene→2-(2-ethoxyphenoxy)-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
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→1,1-Diphenylmethylamine→(2R)-N-(Diphenylmethyl)-1-(4-methoxyphenyl)propan-2-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→(+)-2,2'-Dihydroxy-1,1'-dinaphthyl→(aR)-5,5',6,6',7,7',8,8'-Octahydro[1,1'-binaphthalene]-2,2'-diol→(aR)-4-Chloro-8,9,10,11,12,13,14,15-octahydro-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine→3,5-Dimethylpiperidine→3,5-Dimethylpyridine
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 6total yield: 80g（Tamsulosin Hydrochloride (API)）
(-)-2-(4-Methoxyphenyl)-1-methylethanamine→2-Chloranylethanoyl chloride→2-chloro-N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]acetamide→5-[(2R)-2-(2-chloroacetamido)propyl]-2-methoxybenzene-1-sulfonyl chloride→2-chloro-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→1-Hydroxy-2-ethoxybenzene→2-(2-ethoxyphenoxy)-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
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
Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 3total yield: 18.5g(Tamsulosin Hydrochloride-059)
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→1,1-Diphenylmethylamine→(2R)-N-(Diphenylmethyl)-1-(4-methoxyphenyl)propan-2-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→(+)-2,2'-Dihydroxy-1,1'-dinaphthyl→(aR)-5,5',6,6',7,7',8,8'-Octahydro[1,1'-binaphthalene]-2,2'-diol→(aR)-4-Chloro-8,9,10,11,12,13,14,15-octahydro-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine→3,5-Dimethylpiperidine→3,5-Dimethylpyridine
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 6total yield: 80g（Tamsulosin Hydrochloride (API)）
(-)-2-(4-Methoxyphenyl)-1-methylethanamine→2-Chloranylethanoyl chloride→2-chloro-N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]acetamide→5-[(2R)-2-(2-chloroacetamido)propyl]-2-methoxybenzene-1-sulfonyl chloride→2-chloro-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→1-Hydroxy-2-ethoxybenzene→2-(2-ethoxyphenoxy)-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
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
Dutasteride/Tamsulosin HydrochlorideOptimised routesteps: 3total yield: 18.5g(Tamsulosin Hydrochloride-059)
(4-Methoxyphenyl)acetic acid→1-(4-Methoxyphenyl)-2-propanone→1,1-Diphenylmethylamine→(2R)-N-(Diphenylmethyl)-1-(4-methoxyphenyl)propan-2-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→(+)-2,2'-Dihydroxy-1,1'-dinaphthyl→(aR)-5,5',6,6',7,7',8,8'-Octahydro[1,1'-binaphthalene]-2,2'-diol→(aR)-4-Chloro-8,9,10,11,12,13,14,15-octahydro-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine→3,5-Dimethylpiperidine→3,5-Dimethylpyridine
(-)-2-(4-Methoxyphenyl)-1-methylethanamine→2-Chloranylethanoyl chloride→2-chloro-N-[(2R)-1-(4-methoxyphenyl)propan-2-yl]acetamide→5-[(2R)-2-(2-chloroacetamido)propyl]-2-methoxybenzene-1-sulfonyl chloride→2-chloro-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→1-Hydroxy-2-ethoxybenzene→2-(2-ethoxyphenoxy)-N-[(2R)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]acetamide→(-)-5-[2(R)-[2-(2-Ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide
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→1,1-Diphenylmethylamine→(2R)-N-(Diphenylmethyl)-1-(4-methoxyphenyl)propan-2-amine→(-)-2-(4-Methoxyphenyl)-1-methylethanamine→N-[(2R)-1-(4-Methoxyphenyl)propan-2-yl]acetamide→(+)-2,2'-Dihydroxy-1,1'-dinaphthyl→(aR)-5,5',6,6',7,7',8,8'-Octahydro[1,1'-binaphthalene]-2,2'-diol→(aR)-4-Chloro-8,9,10,11,12,13,14,15-octahydro-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine→3,5-Dimethylpiperidine→3,5-Dimethylpyridine
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