Dimethyl Sulfoxide → Ethyl 4-formylpiperidine-1-carboxylate

Participants

Reaction Steps

A solution of 1.2 eq oxalyl chloride (12.69 g, 0.10 mol) in dichloromethane (150 mL) was cooled to approximately −78° C. and treated dropwise, under nitrogen, with a solution of 2.4 equivalents anhydrous dimethylsulfoxide (15.63 g, 0.20 mol) in dichloromethane (50 mL). 15 min. after the addition was complete, a solution of 1.0 equivalent ethyl 4-(hydroxymethyl)-piperidine-1-carboxylate (D2) (15.60 g, 83.3 mmol) in dichloromethane (50 mL) was added dropwise. 30 minutes after the addition was complete, a solution of 3.0 eq triethylamine

Provenance & Evidence