Preparation of 2-(3-Hydroxy-1-Adamantyl)-2-Oxoacetic Acid: A Key Intermediate for Saxagliptin

Author(s): Jingke Li, Shurong Zhang, Hongrui Zhou, Jun Peng, Yue Feng, Xiangnan Hu

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 5 , 2012


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Abstract:

An optimized synthetic approach to prepare 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid has been reported in a good yield under mild experimental conditions. It was synthesized from 1-adamantanecarboxylic acid via successful reaction with thionyl chloride and sodium diethyl malonate to give dimethyl (1-adamantylcarbonyl) malonate, which was subjected to hydrolysis and decarboxylation by a mixture of acetic acid with water and sulfuric acid and then oxidation by potassium permanganate. The synthesized adamantane derivative was utilized to saxagliptin.

Keywords: 1-Adamantanecarboxylic acid, 1-acetyladamantane, 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid, DPP-IV inhibitor, saxagliptin, insulinotropic, hormone, dipeptidyl, peptidase, a - keto acid

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Article Details

VOLUME: 9
ISSUE: 5
Year: 2012
Published on: 25 May, 2012
Page: [347 - 350]
Pages: 4
DOI: 10.2174/157017812801264755
Price: $65

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