Dimethyl Sulfoxide → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

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Reaction Steps

Dimethyl sulfoxide (7.43 mL, 0.105 mol) was added to oxalyl chloride (5.53 mL, 0.0654 mol) in DCM (244.2 mL) at −78° C. After 10 min, tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (from Aldrich, 10.0 g, 0.0436 mol) in DCM (488.4 mL) was added and the resultant mixture was stirred at −78° C. for 30 min. Triethylamine (30.4 mL, 0.218 mol) was then added and the mixture was stirred for 5 h and the temperature allowed to gradually warm up to RT. After being quenched with water, the mixture was extracted with DCM. The organic layers were combined, washed with brine, dried, and evaporated to dryness. LCMS calculated for C12H21NO3Na(M+Na)+: m/z=250.2; Found: 250.0.

Provenance & Evidence