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

Participants

Reaction Steps

To a stirred solution of 1-boc-3-(hydroxyl)azetine (1.0 g, 5.8 mmol) and triethylamine (1.6 mL, 12 mmol) in CH2Cl2 (10 mL) and DMSO (4 mL) at 0° C. was added pyridine sulfur trioxide (1.8 g, 12 mmol). The reaction was allowed to warm to room temperature. After 18 h, the reaction mixture was partitioned between CH2Cl2 (100 mL) and 1M aqueous citric acid solution (100 mL). The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated to afford tert-butyl 3-oxoazetidine-1-carboxylate as a crude oil. 1H NMR (600 MHz, DMSO-D6) 4.67 (s, 4H); 1.47 (s, 9H).

Provenance & Evidence