1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester monosuccinate ([R-(R*,R*)]-isomer, monoHCl salt)

Base Information

• Chemical Name: 1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester monosuccinate ([R-(R*,R*)]-isomer, monoHCl salt)
• CAS No.: 180468-37-5
• Molecular Formula: C₂₃H₂₆N₂O₂*ClH
• Molecular Weight: 398.933
• Mol file: 180468-37-5.mol

Synonyms:2(1H)-Isoquinolinecarboxylicacid, 3,4-dihydro-1-phenyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester,monohydrochloride, (1R)- (9CI); 2(1H)-Isoquinolinecarboxylic acid,3,4-dihydro-1-phenyl-, 1-azabicyclo[2.2.2]oct-3-yl ester, monohydrochloride,[R-(R*,R*)]-

Chemical Property of 1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester monosuccinate ([R-(R*,R*)]-isomer, monoHCl salt)

Chemical Property:

• Melting Point: 197-199 °C(Solv: acetonitrile (75-05-8); ethyl ether (60-29-7))

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester monosuccinate ([R-(R*,R*)]-isomer, monoHCl salt)

There total 7 articles about 1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester monosuccinate ([R-(R*,R*)]-isomer, monoHCl salt) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

solifenacin (242478-37-1,180272-14-4) → Solifenacin hydrochloride (180468-37-5,180468-40-0)

Guidance literature:

With hydrogenchloride; In methanol; butanone; at 20 ℃; Purification / work up;

Reference yield:

solifenacin (242478-37-1,180272-14-4) → (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate hydrochloride (180468-37-5,180468-40-0)

Guidance literature:

With hydrogenchloride; In ipa; ethanol; at 5 - 30 ℃;

Reference yield:

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8) + (R)-quinuclidin-3-ol (25333-42-0) → Solifenacin hydrochloride (180468-37-5,180468-40-0)

Guidance literature:

(R)-quinuclidin-3-ol; With bis-(p-nitrophenyl) carbonate; In N,N-dimethyl-formamide; at 25 - 30 ℃;

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline; In N,N-dimethyl-formamide; at 25 - 30 ℃; for 3h;

With hydrogenchloride; In water; N,N-dimethyl-formamide; at 25 - 30 ℃; pH=1 - 2;

DOI:10.1007/s00706-011-0610-7

upstream raw materials:

(3S)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinolinecarboxylate

solifenacin

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

(R)-quinuclidin-3-ol

Refernces

• 1、 -. "METHOD FOR THE PREPARATION OF SOLIFENACIN". Page/Page column 3. . Retrieved 2010/06/19.
• 2、 -. "PROCESS FOR PREPARING CHEMICALLY AND CHIRALLY PURE SOLIFENACIN BASE AND ITS SALTS". Page/Page column 40. . Retrieved 2009/09/04.