(S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine

Base Information

• Chemical Name: (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine
• CAS No.: 133099-09-9
• Molecular Formula: C25H24N2O2S
• Molecular Weight: 416.544
• Mol file: 133099-09-9.mol

Synonyms:3-Pyrrolidineacetonitrile,1-[(4-methylphenyl)sulfonyl]-a,a-diphenyl-, (S)-;2,2-Diphenyl-2-((3S)-1-tosyl-3-pyrrolidinyl)acetonitrile;(S)-2,2-Diphenyl-2-(1-tosyl-3-pyrrolidinyl)acetonitrile;

Chemical Property of (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine

Chemical Property:

• Vapor Pressure: 1.43E-13mmHg at 25°C
• Refractive Index: 1.628
• Boiling Point: 582.8 °C at 760 mmHg
• Flash Point: 306.3 °C
• PSA: 69.55000
• Density: 1.241 g/cm³
• LogP: 5.53418
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

3-(S)-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine

There total 5 articles about (S)-3-(1-Cyano-1,1-diphenylmethyl)-1-tosylpyrrolidine 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: 86.5%

(S)-toluene-4-sulfonic acid 1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester → (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile (133099-09-9,133034-03-4)

Guidance literature:

Diphenylacetonitrile; With sodium t-butanolate; In N,N-dimethyl-formamide; at 35 ℃;

(S)-toluene-4-sulfonic acid 1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester; In N,N-dimethyl-formamide; at 20 - 75 ℃; for 4h;

Reference yield: 86.0%

(S)-toluene-4-sulfonic acid 1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester + Diphenylacetonitrile (86-29-3) → (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile (133099-09-9,133034-03-4)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In toluene; at 25 - 60 ℃; for 4.16667 - 6.16667h;

Reference yield:

(+)-3-chloro-1-(toluene-4-sulfonyl)-pyrrolidine (1072227-58-7) + Diphenylacetonitrile (86-29-3) → (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile (133099-09-9,133034-03-4)

Guidance literature:

Diphenylacetonitrile; With potassium hydroxide; In N,N-dimethyl-formamide; for 2h;

(+)-3-chloro-1-(toluene-4-sulfonyl)-pyrrolidine; In N,N-dimethyl-formamide; at 95 - 100 ℃; for 5h;

upstream raw materials:

Diphenylacetonitrile

(+)-3-chloro-1-(toluene-4-sulfonyl)-pyrrolidine

p-toluenesulfonyl chloride

(R)-1-tosylpyrrolidin-3-ol

Downstream raw materials:

(S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetonitrile

(S)-darifenacin hydrobromide

2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide

darifenacin hydrochloride

Refernces

• 1、 -. "IMPROVED PROCESS FOR PRODUCING DARIFENACIN". Page/Page column 7; 10. . Retrieved 2009/11/29.
• 2、 -. "NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF DARIFENACIN, DARIFENACIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS". Page/Page column 13; 24-25. . Retrieved 2008/12/08.