Triethylamine → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

Triethylamine (2.47 mL) was added to a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (0.5 g, 2.9 mmol) in DMSO (5 mL). To this mixture, a solution of pyridine sulphur trioxide (1.8 g, 11.3 mmol) in DMSO (6.5 mL) was added drop-wise and the mixture was stirred at room temperature for 1.5 hrs. The mixture was poured onto ice-water and extracted with ethyl acetate (3×50 mL), organics combined dried with sodium sulfate, filtered and concentrated to afford tert-butyl 3-oxoazetidine-1-carboxylate as white solid (500 mg, 100%). 1H NMR (300 MHz, CDCl3): δ 4.68 (s, 4H), 1.48 (s, 9H).

Provenance & Evidence