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A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid and it's optimization
Hui-Fei Wang1, Run Gan2, Jing Zhou1
1Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Pakistan Journal of Pharmaceutical Sciences
|July 24, 2018
Abstract:
2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid (IV), a key intermediate of saxagliptin for type 2 diabetes mellitus (T2DM), was prepared from 1-adamantanecarboxylic acid(I) via oxidation by potassium permanganate(KMnO4) to afford 3-hydroxy-1-adamantanecarboxylic acid (II), which was treated with a one-pot method to give 1-acetyl-3-hydroxyadamantane (III) followed by oxidation. Some key steps were optimized and the overall yield was about 51%.