Dimethyl Sulfoxide → 1-Boc-piperidine-3-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

Dimethylsulphoxide (1.35 ml, 18.8 mmol) was added dropwise to a solution of oxalyl chloride (1.65 ml, 18.8 mmol) in dichloromethane (20 ml) at −78° C. When the addition was complete, the reaction was stirred for a further 15 minutes at −78° C. 1-(tert-Butoxycarbonyl)-3-(hydroxymethyl)piperidine (2.7 g, 12.6 mmol) was added and the reaction warmed to −20° C. and stirred at this temperature for 20 minutes. Triethylamine (5.25 ml, 37.6 mmol) was added and the reaction allowed to warm to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with water (×2). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was taken up in tetrahydrofuran and filtered through cotton wool. The filtrate was evaporated in vacuo to give the title compound (2.32 g, 89%).

Provenance & Evidence