Dimethyl Sulfoxide → Tert-butyl 3-oxopiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of give N-t-butoxycarbonyl-3-hydroxypiperidine (1.07 g, 5.23 mmol) in 1:1 dimethyl sulfoxide:water (50 ml) is added triethyl amine (3.7 ml) and sulfur trioxide pyridine complex (4.24 g, 26.6 mmol). The reaction mixture is stirred at 25° C. for 3 hrs. The reaction mixture is diluted with ethyl acetate, washed with 1 N KHSO4, water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by flash chromatography (silica gel, 50% ethyl acetate in hexane) to give N-t-butoxycarbonyl-3-ketopiperidine (598 mg).

Provenance & Evidence