1044676-63-2

Basic information

• Product Name: (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile
• Synonyms: (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile
• CAS NO: 1044676-63-2
• Molecular Formula: C17H25N3O2
• Molecular Weight: 303.3993
• Mol File: 1044676-63-2.mol
• Article Data: 45

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile(1044676-63-2)
• EPA Substance Registry System: (2S)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile(1044676-63-2)

Safety Data

• Hazardous Substances Data: 1044676-63-2(Hazardous Substances Data)

Upstream product

• 702-82-9 3-aminoadamantan-1-ol 
• 207557-35-5 (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile 
• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 228244-04-0 tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate 
• 32634-66-5 Di-p-toluoyl-L-tartaric acid 
• 214398-99-9 (S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide 
• 7531-52-4 L-prolinamide 
• 584-08-7 potassium carbonate 
• 79-04-9 chloroacetyl chloride 
• 1119-33-1 (S)-2-Amino-pentanedioic acid 5-ethyl ester 
• 56-86-0 L-glutamic acid 
• 768-95-6 1-adamanthanol 

Downstream Products

• 565453-40-9 vildagliptin carboxylic acid 
• 1789703-37-2 2-(3-hydroxyadamantan-1-yl)-1-imino-hexahydropyrrolo[1,2-a]pyrazin-4-one 
• 1147403-03-9 NVP-BQS867-NX-2 
• 565453-39-6 vildagliptinamide 

Relevant articles and documents

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%.

An economical and facile method to synthesize vildagliptin

A facile and economical synthefic method to prepare vildagliption with-reported.It was started from L proline via succsessful reaction with chloried in tetrahydrofuran to-afford 1(2-chloroacetyl) pyrrolidine-2-carboxylic-acid, followed by reacting with 2-chloro-46-dimethoxy-1,3,5-triazine,N-methylmorpholine and 2,4,6-triazine,N-methlmorpholine-2,4,6-trichloro-1,3,5-triazine-to-give 1-(2-chloroacetyl)-pynolidine 2-carbonitrile which was-reacfed-with 3-aminoadmantanol to get the-forget-compound-of-vildagliption.

PROCESS FOR THE PREPARATION OF VILDAGLIPTIN

The present invention relates to process for the preparation of Vildagliptin. The present invention involves an ecologically friendly process by avoiding the dehydrating agent and use of reagents that are less expensive, easier to handle and its cost effective industrial applicable process.

Continuous preparation method of vildagliptin

The invention discloses a continuous preparation method of vildagliptin, which comprises the following steps: 1, preparing (S)-1-(2-chloracetyl) pyrrolidine-2-carbonitrile from (S)-pyrrolidine-2-carbonitrile p-toluenesulfonate, chloroacetyl chloride, triethylamine and dichloromethane, washing, separating the liquid, and keeping the organic phase; 2, adding water and 3-amino-1-adamantanol into the organic phase, refluxing, evaporating to remove the organic solvent, heating, and reacting to obtain a feed liquid; 3, washing the feed liquid, cooling, adjusting to be acidic, and washing to obtain feed liquid; and 4, carrying out aqueous phase extraction, cooling, adjusting to alkalinity, carrying out liquid separation to reserve an organic phase, carrying out aqueous phase re-extraction, carrying out liquid separation, merging the organic phases, evaporating to remove the solvent, and adding a crystallization solvent to obtain vildagliptin with HPLC purity of 99.5% or more. The raw material provided by the invention is low in water absorption and convenient to prepare, store and feed; through continuous process operation, the operation steps are reduced, and the overall yield is improved; finally, water is used as a reaction solvent, so that the production cost is reduced, the environmental pollution pressure is reduced, and the method is suitable for preparing vildagliptin.