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

Participants

Reaction Steps

A solution of oxalyl chloride (2.4 mL, 27.5 mmol) in 125 mL DCM as cooled to −78 C and DMSO (3.3 mL, 47.1 mmol) was added slowly. After 10 in a solution of 2-(N-tert-butoxycarbonyl-4-piperidyl)ethanol (4.5 grams, 19.6 mol) in 10 mL DCM was added. The mixture was stirred for 20 min then triethylamine (13.6 mL, 98.1 mmol) was added and the mixture was warmed to room temperature. After 30 min the mixture was diluted with ethyl acetate and washed with water (3×). The organic portion was dried over sodium sulfate and concentrated. Flash chromatography (3/1 hexane/EtOAc) afforded 3.7 grams (83%) of the desired aldehyde. 1H NMR (400 MHz, CDCl3). δ1.13-1.43 (m, 2H), 1.48 (s, 9H), 1.68-1.77 (m, 2H), 2.04-2.11 (m, 1H), 2.38-2.41 (d, 2H), 2.71-2.8 (m, 2H), 4.04-4.14 (m, 2H), 9.8 (s, 1H).

Provenance & Evidence