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

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

Volume: 9 Issue: 5

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

Affiliation:

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

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.

Cite this article as:

Li Jingke, Zhang Shurong, Zhou Hongrui, Peng Jun, Feng Yue and Hu Xiangnan, Preparation of 2-(3-Hydroxy-1-Adamantyl)-2-Oxoacetic Acid: A Key Intermediate for Saxagliptin, Letters in Organic Chemistry 2012; 9 (5) . https://dx.doi.org/10.2174/157017812801264755