Dimethyl Sulfoxide → Benzyl 2-methyl-5-oxopiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of oxalyl chloride (13.17 mL, 0.150 mol) in CH2Cl2 (250 mL) at −78° C. was added DMSO (14.23 mL, 0.201 mol) dropwise. The reaction was aged for 20 min at −78° C., then ±Benzyl trans-5-hydroxy-2-methylpiperidine-1-carboxylate (25.0 g, 0.100 mol) was added dropwise over 10 min and aged for an additional 10 min before triethylamine (41.9 mL, 0.301 mol) was added dropwise over 5 min at −78° C. The reaction was warmed to room temperature, then quenched with addition of half-saturated, aqueous NaHCO3 and additional CH2Cl2. The layers were separated, and the organics were dried with MgSO4 and concentrated. The crude material was purified by silica gel gradient chromatography (0-50% ethyl acetate in hexanes), providing ±benzyl 2-methyl-5-oxopiperidine-1-carboxylate.

Provenance & Evidence