1-Benzyloxycarbonyl-3-piperidone → Benzyl 3-hydroxy-3-phenylpiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of 9 ml (9 mmol) phenylmagnesium bromide (1M solution in THF) in THF (13 ml) was added a solution of 1.5 g (6.00 mmol) 3-oxo-piperidine-1-carboxylic acid benzyl ester (commercial) in THF (5 ml) at room temperature over a period of 15 minutes. The mixture was stirred for 30 minutes and then quenched under ice bath cooling with a 20% ammonium chloride solution (4 ml). The organic layer was decanted and the residue was extracted once with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 50%) to provide 0.55 g (30%) of the title compound as a white solid. MS (m/e): 312.0 (M+H+)

Provenance & Evidence