facile method for the synthesis of 2-[3-hydroxy-1-adamantyl]-2-oxoacetic acid and it’s optimization

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%