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

Participants

Reaction Steps

To a stirred solution of oxalyl chloride (4.28 mL, 4.98 mmol) in DCM (5 mL) at −78° C. is added DMSO (0.71 mL, 9.96 mL) dropwise. After stirring for 15 mins tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (0.69 g, 3.69 mmol) is added followed immediately by triethylamine (2.1 mL, 14.75 mmol). The reaction mixture is allowed to warm to room temperature, diluted with DCM (30 mL), washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (Isolute column, eluent: heptane, 0-100% EtOAc) to give 0.19 g of tert-butyl 3-formylazetidine-1-carboxylate (27%).

Provenance & Evidence