133099-09-9

Basic information

• Product Name: (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine
• Synonyms: (s)-3-(1-cyano-1,1-diphenylmethyl)-1-tosyloxypyrrolidine (Darifenacin);(3S)- 1-[(4-methylphenyl)sulfonyl]-diphenyl-3-Pyrrolidineacetonitrile;(s)-3-(1-cyano-1,1-diphenylmethyl)-1-tosyloxypyrrolidine;(S)-2,2-Diphenyl-2-(1-tosyl-3-pyrrolidinyl)acetonitrile;(S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine;3-(S)-(1-cayano-1,1-diphenylmethyl)-1-tosylpyrrolidine;(S)-3-(1-Cyano-1,1-d;(S)-3-(1-Cyano-1,1-diphenylMethyl)-1-tosylpyrrolid
• CAS NO: 133099-09-9
• Molecular Formula: C₂₅H₂₄N₂O₂S
• Molecular Weight: 416.54
• EINECS: 1312995-182-4
• Product Categories: APIs Intermediate;Benzenes
• Mol File: 133099-09-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 582.8 °C at 760 mmHg
• Flash Point: 306.3 °C
• Appearance: /
• Density: 1.241
• Vapor Pressure: 1.43E-13mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine(133099-09-9)
• EPA Substance Registry System: (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine(133099-09-9)

Safety Data

• Hazardous Substances Data: 133099-09-9(Hazardous Substances Data)

Usage

Uses

(3S)-1-Tosyl-α,α-diphenyl-3-pyrrolidineacetonitrile is a reactant used in the preparation of Darifenacin Hydrobromide (D193400), which is used as a medication to treat urinary incontinence. It works by blocking the M3 muscarinic acetylcholine receptor.

InChI:InChI=1/C25H24N2O2S/c1-20-12-14-24(15-13-20)30(28,29)27-17-16-23(18-27)25(19-26,21-8-4-2-5-9-21)22-10-6-3-7-11-22/h2-15,23H,16-18H2,1H3/t23-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 133034-00-1 (R)-1-tosylpyrrolidin-3-ol 
• 1072227-58-7 (+)-3-chloro-1-(toluene-4-sulfonyl)-pyrrolidine 
• 86-29-3 Diphenylacetonitrile 

Downstream Products

• 133099-11-3 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile 
• 133099-07-7 (S)-darifenacin hydrobromide 
• 134002-25-8 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide 
• 586346-94-3 darifenacin hydrochloride 
• 133099-04-4 darifenacin 

Relevant articles and documents

IMPROVED PROCESS FOR PRODUCING DARIFENACIN

The present invention discloses an improved process for producing darifenacin, the process comprising decarboxylating (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid followed by in situ tosylation to give l-tosyl-3-(R)-(-)-hydroxypyrrolidine, tosylating the l-tosyl-3-(R)-(-)-hydroxypyrrolidine with methyl-p-toluenesuolphonate to give l-tosyl-3- (S)-(-)-tosyloxy pyrrolidine, reacting l-tosyl-3-(S)-(-)-tosyloxy pyrrolidine with diphenyl acetonitrile in presence of a base to give 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine, de-protecting 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl)-l- tosylpyrrolidine in the presence of phenol in acidic medium to give 3-(S)-(+)-(l-cyano- 1,1-diphenylmethyl) pyrrolidine, hydrolyzing 3-(S)-(+)-(l-cyano-l,l-diphenylmethyl) pyrrolidine followed by salt formation to obtain 3-(S)-(+)-(l-carbamoyl-l,l- diphenylmethyl)pyrrolidine.L-(+)-tartrate, condensing 3-(S)-(+)-( 1 -carbamoyl- 1,1- diphenylmethyl)pyrrolidine-L(+)-tartrate with 5-(2-bromoethyl)-2,3-dihydrobenzofuran employing a base in a solvent to give darifenacin.

NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF DARIFENACIN, DARIFENACIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to novel and improved processes for the preparation of intermediates of darifenacin, darifenacin and its pharmaceutically acceptable salts. Darifenacin is chemically known as 3 -(S)-(-)-(l -carbamoyl- 1,1 -diphenylmethyl)-l- [2- (2,3-dihydro benzofuran-5-yl)ethyl]pyrrolidine and represented by formula-2. The invention also relates to the novel polymorphs of the pharmaceutically acceptable salts of darifenacin and the methods for their re aration.

PROCESSES FOR PREPARING DARIFENACIN HYDROBROMIDE

The invention encompasses processes for the preparation of darifenacin hydrobromide.