A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid and it's optimization.

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%.