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Letters in Organic Chemistry
ISSN (Print): 1570-1786
ISSN (Online): 1875-6255
VOLUME: 11
ISSUE: 8
DOI: 10.2174/1570178611666140421231237      Price:  $58









A Convenient Method for the Synthesis of (S)-N-boc-3-hydroxyadamantylglycine: A Key Intermediate of Saxagliptin

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Author(s): Anmin Wang, Yu Deng, Xinmei Pan, Yingjie Chen, Zhu Tao, Dinghua Liang and Xiangnan Hu
Pages 627-631 (5)
Abstract:
(S)-N-Boc-3-Hydroxyadamantylglycine is a key intermediate of saxagliptin. It was synthesized from 1- adamantanecarboxylic acid to afford 1-acetyladamantane (2), which was converted into 2-(1-adamantyl)-2-oxoacetic acid (3) through oxidation, and then into 1-adamantyl-2-hydroxyimino acetic acid (4) followed by treatment of hydroxylamine hydrochloride, then 4 was reducted and Boc-protected to give N-Boc-adamantylglycine (5), which was oxidized with KMnO4 and treated with a chiral base. Utilizing this route, (S)-N-Boc-3-Hydroxyadamantylglycine was prepared. This work is to elaborate a convenient route to synthesize (S)-N-Boc-3-Hydroxyadamantylglycine and provide a new idea for the synthesis of saxagliptin.
Graphical Abstract:
Keywords:
Boc-protection, reduction, (S)-N-Boc-3-Hydroxyadamantylglycine, saxagliptin, synthesis, treatment.
Affiliation:
Department of Pharmacy, Chongqing Medical University, 400016, Chongqing. P.R. China.