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

作者：Wang Anmin; Deng Yu; Pan Xinmei; Chen Yingjie; Tao Zhu; Liang Dinghua; Hu Xiangnan^*

来源：Letters in Organic Chemistry, 2014, 11(8): 627-631.

DOI：10.2174/1570178611666140421231237

• Boc-protection
• reduction
• (S)-N-Boc-3-Hydroxyadamantylglycine
• saxagliptin
• synthesis
• treatment

(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.

• 出版日期2014
• 单位重庆医科大学