Dimethyl Sulfoxide → tert-Butyl 3-oxo-2-phenylpiperidine-1-carboxylate

Participants

Reaction Steps

Oxalyl chloride (1 ml) was added dropwise to a solution of methyl sulphoxide (0.82 ml) in anhydrous dichloromethane (4 ml) at -78° C. under a nitrogen atmosphere. A solution of 1-t-butoxycarbonyl-3-hydroxy-2-phenyl piperidine (1.6 g, Example 2c) in anhydrous dichloromethane (10 ml) was added, and the reaction stirred for 1.75 h before triethylamine (4 ml) was added and the reaction allowed to warm to room temperature. The reaction was partitioned between ethyl acetate and water, the organic phase washed with brine, dried and evaporated in vacuo to provide 1-t-butoxycarbonyl-2-phenylpiperidin-3-one as an oil.

Provenance & Evidence