Dimethyl Sulfoxide → tert-Butyl 3-(3-oxopropyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

An oven-dried 3-neck 1 L round-bottom flask under nitrogen was charged with DCM (100 mL) and oxalyl chloride (1.98 mL, 22.6 mmol) and cooled to −60° C. DMSO (3.21 mL, 45.2 mmol) was added dropwise, and the reaction mixture was stirred for 5 min. A solution of tert-butyl 3-(3-hydroxypropyl)piperidine-1-carboxylate (5.00 g, 20.6 mmol) in DCM (100 mL) was added via addition funnel, and the reaction mixture was stirred for 20 min. TEA (14.3 mL, 103 mmol) was added, and the reaction mixture was warmed slowly to RT. The reaction mixture was poured into 2.5% NaHCO3 and extracted with methylene chloride. The combined organic layers were washed with 5% KHSO4 then brine, dried with anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel chromatography (80 hexane/20 EtOAc). LRMS (M+H)+=242.3.

Provenance & Evidence