A Facile and Economical Method to Synthesize Vildagliptin

Wang, An Min; Tao, Zhu; Chen, Yingjie; Pan, Xinmei; Hu, Xiangnan

doi:10.2174/1570178611666140922121805

Cited by 3 publications

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“… [ α ] normalD 20 = −0.09 ( c 1 g/100 mL, MeOH) (literatur 25 — [ α ] normalD 20 = −0.087 ( c 1 g/100 mL, MeOH)); The 1 H and 13 C NMR data of this compound are in good agreement with the reported data. 11…”

Section: Methodsmentioning

confidence: 99%

“…3-Aminoadamantanol ( 3 ) and ( S )-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile ( 2 ) are important compounds because of their key roles in the synthesis of vildagliptin (Scheme 1). 10 In terms of the relevant literature, synthetic methods toward these intermediates have disadvantages of expensive starting materials, 11 complex synthetic routes, and low yields. Therefore, it is necessary to develop simple methods with good yields in order to obtain rapidly vildagliptin intermediates.…”

Section: Introductionmentioning

confidence: 99%

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A facile method to synthesize vildagliptin

Zhang

Jiang

Guan

et al. 2020

Journal of Chemical Research

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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%.

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