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

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl 3-oxopiperidine-1-carboxylate (2.33 g, 10 mmol) in dry THF (50 mL) at −78° C. was added MeMgBr (3.6 mL, 3M solution in THF, 11 mmol) slowly. The reaction was allowed to stir at −78° C. for 10 min then slowly warmed to r.t. The reaction was quenched with NH4Cl and dissolved in EtOAc (300 mL) and washed with saturated NH4Cl and brine, dried and filtered, and concentrated to give the crude. The crude material was further purified by silica gel chromatography to yield benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate. (53% yield). LCMS (m/z): 250.1 (MH+); LC Rt=2.98 min.

Provenance & Evidence