CAS 25333-42-0

(R)-quinuclidin-3-ol

Codes: ACLI-004, SOLIF-004

Application context (from source-drug indications)

Chronic obstructive pulmonary diseaseAclidinium Bromide/Formoterol Fumarate DihydrateLower 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 HydrochlorideChronic obstructive pulmonary diseaseAclidinium BromideOveractive bladderSolifenacin SuccinateUrge incontinenceSolifenacin SuccinateUrinary tract diseaseSolifenacin Succinate

Source drugs (routes using this intermediate)

Drug	Tier	Expiry
Aclidinium Bromide/Formoterol Fumarate Dihydrate	Tier C — Watch / trade	-
Solifenacin Succinate/Tamsulosin Hydrochloride	Tier C — Watch / trade	-
Aclidinium Bromide	Tier C — Watch / trade	-
Solifenacin Succinate	Tier B — Position early	-

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.

Aclidinium Bromide/Formoterol Fumarate DihydrateOriginator routesteps: 3total yield: 7.2 g

dimethyl oxalate→2-bromothiophene→methyl 2-hydroxy-2,2-di(thiophen-2-yl)acetate→(R)-quinuclidin-3-ol→(1S,3R,4S)-quinuclidin-3-yl 2-hydroxy-2,2-di(thiophen-2-yl)acetate→(3-bromopropoxy)benzene

Solifenacin Succinate/Tamsulosin HydrochlorideOriginator routesteps: 2total yield: 10.1 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→ethyl carbonochloridate→ethyl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate→(R)-quinuclidin-3-ol

Solifenacin Succinate/Tamsulosin HydrochlorideProcess routesteps: 3total yield: 270 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→bis(4-nitrophenyl) carbonate→(R)-4-nitrophenyl quinuclidin-3-yl carbonate→succinic acid

Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 5total yield: 142.8 mg

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane→ethyl(phenyl)zinc→3,4-dihydroisoquinoline 2-oxide→tert-butyl ((2S,3S)-3-methyl-1-morpholinopentan-2-yl)carbamate→(S)-1-phenyl-3,4-dihydroisoquinolin-2(1H)-ol→4-nitrophenyl carbonochloridate→4-nitrophenyl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Solifenacin Succinate/Tamsulosin HydrochlorideProcess routesteps: 3total yield: 390.2 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→succinic acid→perfluorophenyl (2,3,4,5-tetrafluorophenyl) carbonate→(R)-perfluorophenyl quinuclidin-3-yl carbonate

Solifenacin Succinate/Tamsulosin HydrochlorideOptimised routesteps: 2total yield: 1.1 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→1-bromopropane→propyl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Aclidinium BromideOriginator routesteps: 3total yield: 7.2 g

Solifenacin SuccinateOriginator routesteps: 2total yield: 10.1 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→ethyl carbonochloridate→ethyl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate→(R)-quinuclidin-3-ol

Solifenacin SuccinateProcess routesteps: 3total yield: 270 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→bis(4-nitrophenyl) carbonate→(R)-4-nitrophenyl quinuclidin-3-yl carbonate→succinic acid

Solifenacin SuccinateOptimised routesteps: 5total yield: 142.8 mg

Solifenacin SuccinateProcess routesteps: 3total yield: 390.2 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→succinic acid→perfluorophenyl (2,3,4,5-tetrafluorophenyl) carbonate→(R)-perfluorophenyl quinuclidin-3-yl carbonate

Solifenacin SuccinateOptimised routesteps: 2total yield: 1.1 g

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline→(R)-quinuclidin-3-ol→1-bromopropane→propyl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

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