An Improved Synthetic Method of Saxagliptin Intermediate 3-Hydroxy-1- acetyladamantane and Its Characterization

Author(s): Run Gan, Jing Zhou, Jie Li, Ming Zhang, Xue Jiang, Xiangnan Hu.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 7 , 2016

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Abstract:

An improved method with high yield and simple steps for the synthesis of 3-hydroxy-1-acetyladamantane was reported. 3-Hydroxy-1-acetyladamantane is an important intermediate of Saxagliptin for type 2 diabetes mellitus (T2DM). Its synthetic method started from 1-adamantanecarboxylic acid via oxidation by sulfuric acid/nitric acid, then VHA reagent (SOCl2/DMF) and sodium diethyl malonate were used in one-pot through acylation, substitution, decarboxylation and alkalization to give the target compound. It is an improved method that VHA reagent (SOCl2/DMF) was used in the step of acylation which effectively enhanced the total yield up to 74%, and the operations were effectually simplified by the one-pot method. The synthesized target compound has been characterized by single-crystal X-ray diffraction. The single-crystal X-ray diffraction analysis demonstrates that the target compound has extensive intermolecular hydrogen bondings involving the hydroxyl and acetyl groups in the solid state and the structure of the target compound was proved as 3-hydroxy-1-acetyladamantane.

Keywords: 3-hydroxy-1-acetyladamantane, Saxagliptin, intermediate, one-pot method, single-crystal X-ray diffraction.

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Article Details

VOLUME: 13
ISSUE: 7
Year: 2016
Page: [514 - 518]
Pages: 5
DOI: 10.2174/1570178613666160830160805
Price: $58

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