207557-35-5

Basic information

• Product Name: (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile
• Synonyms: (2S)-1-(2-Chloroacetyl)-2-9-pyrrolidinecarbonitrile;Vildagliptin interMediate C;vildagliptin Impurity J;cas:207557-35-5;2-Pyrrolidinecarbonitrile, 1-(chloroacetyl)-, (2S)-;(S)-1-(2-CHLOROACETYL)PYRROLIDINE-2-CARBONITRILE;(2S)-1-(CHLOROACETYL)-2-PYRROLIDINECARBONITRILE;(2S)-1-CHLOROACETYLPYRROLIDINE-2-CARBONITRILE
• CAS NO: 207557-35-5
• Molecular Formula: C₇H₉ClN₂O
• Molecular Weight: 172.61
• EINECS: 1592732-453-0
• Product Categories: Pharmaceuticalintermediates;ACETYLHALIDE;intermediate
• Mol File: 207557-35-5.mol
• Article Data: 57

Chemical Properties

• Melting Point: 52-53 °C
• Boiling Point: 363.149 °C at 760 mmHg
• Flash Point: 173.427 °C
• Appearance: /
• Density: 1.273 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: -4.65±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile(207557-35-5)
• EPA Substance Registry System: (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile(207557-35-5)

Safety Data

• Hazardous Substances Data: 207557-35-5(Hazardous Substances Data)

Usage

Description

(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile, also known as (2S)-1-(2-Chloroacetyl)-2-pyrrolidinecarbonitrile, is a white crystalline compound that serves as a crucial intermediate in the synthesis of pharmaceuticals. It is characterized by its unique molecular structure, which includes a chloroacetyl group and a pyrrolidinecarbonitrile moiety, making it a valuable building block for the development of various drugs.

Uses

Used in Pharmaceutical Industry:
(2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile is used as a key intermediate for the synthesis of dipeptidyl peptidase IV (DPP-IV) inhibitors, specifically for the production of Vildagliptin (V305000). This application is significant because DPP-IV inhibitors play a vital role in managing type 2 diabetes by reducing blood glucose levels and improving insulin sensitivity.
As a result, (2S)-1-(Chloroacetyl)-2-pyrrolidinecarbonitrile is essential in the development of medications that help control and manage diabetes, offering a promising avenue for the treatment of this prevalent metabolic disorder.

InChI:InChI=1/C7H9ClN2O/c8-4-7(11)10-3-1-2-6(10)5-9/h6H,1-4H2/t6-/m0/s1

Upstream product

• 96166-39-1 1-glycoloyl-L-proline amide 
• 79-04-9 chloroacetyl chloride 
• 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 
• 56-86-0 L-glutamic acid 
• 204387-53-1 (2S)-pyrrolidine-2-carbonitrile 
• 79-11-8 chloroacetic acid 
• 204387-54-2 (2S)-pyrrolidine-2-carbonitrile 4-methylbenzene-1-sulfonic acid 
• 42429-27-6 L-prolinamide hydrochloride 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 23500-10-9 (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid 
• 7531-52-4 L-prolinamide 

Relevant articles and documents

Synthesis of main impurity of vildagliptin

A four-step synthesis of the main impurity of vildagliptin has been easily accomplished with high-yielding starting from L-proline. This compound can be used as a reference marker in an analytical method to determine the chemical purity of the vildagliptin.

Bis-morpholinophosphorylchloride, a novel reagent for the conversion of primary amides into nitriles

Bis-morpholinophosphorylchloride (Bmpc), in the presence of a base, is an efficient dehydrating agent for both aromatic and aliphatic primary amides, and gives corresponding nitriles under mild conditions in god yields and purity. During the reaction the enantiomeric integrity remains intact.

Preparation method of high chiral purity (S)-1-(2-chloracetyl) pyrrolidine-2-formonitrile

The invention discloses a preparation method of high chiral purity (S)-1-(2-chloracetyl) pyrrolidine-2-formonitrile, the preparation method comprises: S1, in the presence of a solvent and an acid-binding agent, carrying out a coupling reaction on L-proline and chloracetyl chloride to obtain an intermediate I; s2, in the presence of a solvent and sodium iodide, carrying out cyclization reaction on the intermediate I in an alkaline environment to obtain an intermediate II; s3, in the presence of a solvent and an ammonolysis agent, carrying out ammonolysis ring-opening reaction on the intermediate II to obtain an intermediate III; and S4, in the presence of a solvent and phosphorus oxychloride, carrying out chlorination and dehydration reaction on the intermediate III to obtain (S)-1-(2-chloracetyl) pyrrolidine-2-formonitrile. The method has the advantages of high chiral purity, simple steps, easily available and cheap raw materials, convenient post-treatment and high yield, and is suitable for industrial production.

A facile method to synthesize vildagliptin

An efficient and high-yielding synthetic method for the preparation of vildagliptin via four steps is reported. The process starts from L-proline and involves a successful reaction with chloroacetyl chloride in tetrahydrofuran to afford (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid, followed by a reaction with acetonitrile in the presence of sulfuric acid to give (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile. This is then reacted with 3-aminoadamantanol to give vildagliptin. 3-Aminoadamantanol is prepared from 1-aminoadamantane hydrochloride via oxidation with sulfuric acid/nitric acid and boric acid as the catalyst followed by ethanol extraction. The overall yield is 95%.