抄録
In the course of investigation of selective ligands for opioid receptor, we discovered a oxidative reaction of tertiary amine to amide with osmium tetraoxide. As this reaction with osmium tetraoxide has not yet been reported, we examined it in details. Osmium tetraoxide catalyzed oxidation of compound 1 in the presence of potassium ferricyanide as a cooxidant gave ketoamide 2 (44%) and hydroxyamide 3 (40%) as major products. Next, to investigate the scope of the oxidation, N-alkyl-4-arylpiperidines were subjected to the same oxidation conditions to afford amide and hydroxyamide. Here, we present the oxidative reaction and its plausible mechanism in details.
