ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)
Volume 12, 10 Issues, 2015
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A Convenient Method for the Synthesis of (S)-N-boc-3-hydroxyadamantylglycine: A Key Intermediate of Saxagliptin
Letters in Organic Chemistry, 11
): 627-631.Author(s): Anmin Wang
, Yu Deng
, Xinmei Pan
, Yingjie Chen
, Zhu Tao
, Dinghua Liang
and Xiangnan Hu
Department of Pharmacy, Chongqing Medical University, 400016, Chongqing. P.R. China.
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.
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