134002-26-9

Basic information

• Product Name: 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate
• Synonyms: (S)--Diphenyl-3-pyrrolidine acetamide L-Tartaric Acid Salt;(S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide L-tartaric acid salt;Darifenacin Intermediate 5;(S)-α,α-Diphenyl-3-pyrrolidine acetamide L-Tartaric;Darifenacin Intermediate 8;(S)-Alpha,Alphal-Diphenyl-3-Pyrrolidineacetamide tartrate;3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate;(S)-Alpha,Alpha-Diphenyl-3-Pyrrolidine Acetamide-L-Tartrate
• CAS NO: 134002-26-9
• Molecular Formula: C22H26N2O7
• Molecular Weight: 430.45104
• EINECS: 1312995-182-4
• Product Categories: Pharmaceutical material and intermeidates;INTERMEDIATESOFDARIFENACIN;API intermediates;Benzenes
• Mol File: 134002-26-9.mol
• Article Data: 9

Chemical Properties

• Appearance: White powder
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Water (Slightly)
• CAS DataBase Reference: 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate(134002-26-9)
• EPA Substance Registry System: 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate(134002-26-9)

Safety Data

• Hazardous Substances Data: 134002-26-9(Hazardous Substances Data)

Usage

Description

3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate is a complex organic compound with a unique molecular structure. It is characterized by its chiral center, which gives it specific stereochemical properties. 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate is derived from the synthesis of Darifenacin, a medication used to treat overactive bladder, and is also known to exhibit muscarinic receptor antagonist activity.

Uses

Used in Pharmaceutical Industry:
3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate is used as an impurity in the synthesis of Darifenacin (D193500), a medication for overactive bladder. Its presence in the synthesis process is crucial for the development of the final drug product, as it can impact the efficacy and safety of the medication.
Additionally, 3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrroloidine-L-(+)-tartarate is used as a muscarinic receptor antagonist. This application is significant in the field of pharmacology, as muscarinic receptor antagonists play a vital role in treating various conditions, such as overactive bladder, asthma, and chronic obstructive pulmonary disease (COPD). The compound's ability to block muscarinic receptors can help alleviate symptoms and improve the quality of life for patients suffering from these conditions.

InChI:InChI=1/C18H20N2O.C4H6O6/c19-17(21)18(16-11-12-20-13-16,14-7-3-1-4-8-14)15-9-5-2-6-10-15;5-1(3(7)8)2(6)4(9)10/h1-10,16,20H,11-13H2,(H2,19,21);1-2,5-6H,(H,7,8)(H,9,10)/t16-;1-,2-/m11/s1

Upstream product

• 134002-25-8 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide 
• 87-69-4 L-Tartaric acid 
• 133099-11-3 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile 
• 1189753-52-3 (S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile 
• 87-69-4 tartaric acid 

Downstream Products

• 586346-94-3 darifenacin hydrochloride 

Relevant articles and documents

A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr

Darifenacin is a potent and competitive M3 selective receptor antagonist (M3SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).

PROCESS FOR PREPARING 3-SUBSTITUTED PYRROLIDINE COMPOUNDS

Disclosed is a process for preparing 3 -substituted pyrrolidine compounds of formula (VII) or salts thereof, wherein R1 is described herein, which are intermediate compounds useful for the synthesis of darifenacin which is indicated for the treatment of overactive bladder with symptoms of urge, urinary incontinence, and the like, and pharmaceutically acceptable salts thereof. Also disclosed is a process for preparing darifenacin and pharmaceutically acceptable salts thereof.

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.