204387-53-1

Basic information

• Product Name: (S)-PYRROLIDINE-2-CARBONITRILE
• Synonyms: (2S)-pyrrolidine-2-carbonitrile;2-Pyrrolidinecarbonitrile, (2S)-;(S)-2-Cyanopyrrolidine TFA;(2S)-2-Pyrrolidinecarbonitrile;(2S)-2-Cyanopyrrolidin-1-ium 2,2,2-trifluoroacetate;(2S)-pyrrolidine-2-carbonitrile trifluoroacetate;Vildagliptin Impurity 5;(S)-2-Cyanopyrrolidine trifluoroacetic acid
• CAS NO: 204387-53-1
• Molecular Formula: C₅H₈N₂
• Molecular Weight: 96.1322
• Mol File: 204387-53-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 208.9±33.0 °C(Predicted)
• Appearance: /
• Density: 1.01±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 7.06±0.10(Predicted)
• CAS DataBase Reference: (S)-PYRROLIDINE-2-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-PYRROLIDINE-2-CARBONITRILE(204387-53-1)
• EPA Substance Registry System: (S)-PYRROLIDINE-2-CARBONITRILE(204387-53-1)

Safety Data

• Hazardous Substances Data: 204387-53-1(Hazardous Substances Data)

Usage

Description

(S)-PYRROLIDINE-2-CARBONITRILE, also known as (2S)-2-Pyrrolidinecarbonitrile, is an organic compound with the molecular formula C5H8N2. It is a chiral molecule with a pyrrolidine ring and a nitrile group, and it exists in two enantiomeric forms, (S) and (R). The (S) form is the one being discussed here. It is a versatile building block in organic synthesis and has potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
(S)-PYRROLIDINE-2-CARBONITRILE is used as a key intermediate in the synthesis of glutamic acid derivatives. These derivatives have been found to be potent dipeptidyl peptidase inhibitors, which are important in the development of drugs for the treatment of various diseases, such as type 2 diabetes, obesity, and other metabolic disorders.
In the pharmaceutical industry, (S)-PYRROLIDINE-2-CARBONITRILE plays a crucial role in the development of novel therapeutic agents. Its unique structure allows for the creation of compounds with specific biological activities, making it a valuable component in the design and synthesis of new drugs.
Additionally, due to its chiral nature, the (S) enantiomer may exhibit different biological activities compared to its (R) counterpart. This makes it an interesting target for research and development, as the specific enantiomer can be used to target specific biological pathways or receptors, potentially leading to more effective and selective treatments.

Upstream product

• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 7531-52-4 L-prolinamide 
• 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate 
• 147-85-3 L-proline 
• 7677-24-9 trimethylsilyl cyanide 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 56-86-0 L-glutamic acid 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 

Downstream Products

• 864921-20-0 (S)-3-tert-Butoxycarbonylamino-4-((S)-2-cyano-pyrrolidin-1-yl)-4-oxo-butyric acid benzyl ester 
• 680227-80-9 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4-iodo-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872342-03-5 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4-furan-2-yl-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872341-97-4 [(S)-1-Biphenyl-4-ylmethyl-2-((S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872341-98-5 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4'-methyl-biphenyl-4-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872342-01-3 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(2'-fluoro-biphenyl-4-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872342-00-2 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(4'-fluoro-biphenyl-4-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872342-02-4 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(2',4'-difluoro-biphenyl-4-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 872341-99-6 [(S)-2-((S)-2-Cyano-pyrrolidin-1-yl)-1-(3',4'-dimethoxy-biphenyl-4-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Evidence and exploitation of dicationic ammonium-nitrilium superelectrophiles: direct synthesis of unsaturated piperidinones

Exploiting superacid activation, the reactivity of aminonitriles was enhanced through the transient formation of highly reactive ammonium-nitrilium superelectrophiles. Demonstrated by usingin situlow-temperature NMR experiments and confirmed by X-ray diffraction analysis, these dications can be intramolecularly trapped by non-activated alkenes to generate unsaturated piperidinones, including enantioenriched ones, in a straightforward way.

Evaluation of Amino Nitriles and an Amino Imidate as Organo?-catalysts in Aldol Reactions

The efficiency of l -valine and l -proline nitriles and a tert -butyl?- l -proline imidate as organocatalysts for the aldol reaction have been evaluated. l -Valine nitrile was found to be a syn -selective catalyst, while l -proline nitrile was found to be anti -selective, and gave products in modest to good enantioselectivities. tert -Butyl l -proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti -selectivity. The enantioselectivity of the tert -butyl l -proline imidate was found to be good to excellent, with products being formed in up to 94percent enantiomeric excess.

Preparation method of intermediate of medicine vildagliptin for treating type 2 diabetes

The invention discloses a preparation method of an intermediate of a medicine vildagliptin for treating type 2 diabetes. The preparation method comprises the steps that 1, 2-carboxyl pyrrolidine and N-phthalimide are subjected to condensation to obtain a compound shown as the formula I which is shown in the description; 2, in the presence of tris(2-phenylpyridine)iridium, silver bromide and a compound shown as the formula II, the compound shown as the formula I and trimethylsilyl cyanide are subjected to heating reaction to obtain (S)-2-cyanopyrrolidine; 3, the (S)-2-cyanopyrrolidine is reacted with chloroacetyl chloride to obtain the vildagliptin intermediate (S)-1-(2-chloracetyl)-2-cyanopyrrolidine. According to the preparation method, the adopted raw materials are wider in resource, thereaction is high in selectivity and yield, the chiral target compound is obtained, the conditions are mild, and the method is easy to implement.