Dimethyl Sulfoxide → Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of trimethylsulfoxonium iodide (2.17 g), sodium hydride (oil, 60%, 395 mg) and dimethyl sulfoxide (20 mL) was stirred at room temperature for 1 hr, and benzyl 4-(2-oxoethoxy)piperidine-1-carboxylate (2.28 g) was added thereto. The obtained mixture was stirred at room temperature for 3 days. Water was added thereto, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (208 mg).

Provenance & Evidence