732228-02-3

Basic information

• Product Name: (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
• Synonyms: (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester
• CAS NO: 732228-02-3
• Molecular Weight: 362.472
• Mol File: 732228-02-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester(732228-02-3)
• EPA Substance Registry System: (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester(732228-02-3)

Safety Data

• Hazardous Substances Data: 732228-02-3(Hazardous Substances Data)

Usage

Description

(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester, also known as (1S,3S)-Solifenacin, is an organic compound that serves as an intermediate in the synthesis of pharmaceuticals. It is characterized by its unique molecular structure, which includes an isoquinolinecarboxylic acid core and a 1-azabicyclo[2.2.2]oct-3-yl ester group. (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester plays a crucial role in the development of medications for specific medical conditions.

Uses

Used in Pharmaceutical Industry:
(1S,3S)-Solifenacin is used as an intermediate in the synthesis of (1S,3’S)-Solifenacin Succinate (S676730), which is a muscarinic M3 receptor antagonist. This makes it a valuable component in the development of medications for the treatment of urinary incontinence. By targeting the muscarinic M3 receptors, (1S,3’S)-Solifenacin Succinate helps to control the involuntary contractions of the bladder, thereby reducing episodes of incontinence and improving the quality of life for patients suffering from this condition.

Upstream product

• 180468-42-2 (S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 3278-14-6 N-phenethylbenzamide 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 1619-34-7 3-quinuclidinol 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1035547-81-9 (3R)-1-azabicyclo[2.2.2]oct-3-yl (1S)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate hydrogen L-tartrate 
• 862207-71-4 (1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate 
• 862207-70-3 (3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate 
• 1262506-09-1 solifenacin succinate 

Relevant articles and documents

An improved process for the preparation of highly pure solifenacin succinate via resolution through diastereomeric crystallisation

An improved process for the preparation of solifenacin succinate (1) involving resolution through diastereomeric crystallization is described. (1S)-IQL derivative (5) is esterified to form (1S)-ethoxycarbonyl IQL derivative (6) which is condensed with (RS)-3-quinuclidinol (7) to form a solifenacin diastereomeric mixture (8); this is subjected to resolution through diastereomeric crystallization to produce solifenacin succinate (1), which is used for the treatment of an overactive bladder.

NOVEL PROCESS FOR THE PREPARATION OF SOLIFENACIN SUCCINATE

The present invention relates to a process for the preparation of Solifenacin succinate by condensing a compound of formula (IVb) with (RS)-3-quinuclidinol, wherein, R represents methyl, ethyl, isopropyl; to produce a diastereomeric mixture of ( 1S)-3,4-dihydro- 1 -phenyl-2( 1 H)-isoquinolinecarboxylic acid (3RS)- 1 - azabicyclo[2.2.2]oct-3-yl ester, which is treated with succinic acid in a solvent or mixture of solvents to produce optically pure Solifenacin succinate, Formula (X).

PROCESS FOR THE PREPARATION OF SOLIFENACIN

A process for the preparation of (1S)-QR)-I -azabicyclo[2.2.2.]oct-3-yl 3,4-dihydro-1-phenyl- 2(1H)-isoquino-line carboxylate by reacting (1S)-alkyl 1-phenyl-1,2,3,4-tetrahydro-2-isoquinoline carboxylate with 3-(R)-quinuclidol in an inert solvent, where a primary alkyl ester of the carboxylate whose alkyl length is C1-C4 is used and the reaction is catalyzed by a non-nu-cleophilic base.