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

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

Used in Pharmaceutical Industry:
(S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine is used as a key reactant in the preparation of Darifenacin Hydrobromide (D193400), a medication used to treat urinary incontinence. Darifenacin Hydrobromide works by selectively blocking the M3 muscarinic acetylcholine receptor, which helps to control involuntary muscle contractions in the bladder.
In the synthesis of Darifenacin Hydrobromide, (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine serves as a crucial building block, providing the necessary chiral center and structural features required for the final product. (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine's unique properties and reactivity make it an essential component in the development of this medication, contributing to its effectiveness in managing urinary incontinence.

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

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

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

SUBSTITUTED PYRROLIDINES

Disclosed herein are substituted pyrrolidine-based muscarinic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

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.

PREPARATION OF DARIFENACIN AND ITS SALTS

Provided are various processes and compounds related to darifenacin and/or its salts. For example, there is provided a process for preparing a free base of darifenacin: Formula, or the salt thereof, the process including reacting 3-(S)-(cyanodiphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl) ethyl] pyrrolidine of the Formula (IV), or a salt thereof: Formula (IV) with a base effective to convert the nitrile group of the compound of the Formula (IV) to the amide group of the darifenacin in an organic solvent, the reaction being carried out in the organic solvent, with a proviso that the solvent is not 2-methyl-butan-2-ol, and with further proviso that the reaction produces less than about 0.5 % of the compound of the Formula (Ic): Formula (Ic) in the reaction mass, as measured by HPLC. Various embodiments and variants are provided.

PROCESSES FOR PREPARING DARIFENACIN HYDROBROMIDE

The invention encompasses processes for the preparation of darifenacin hydrobromide.