Dimethyl Sulfoxide → tert-butyl N-(2-oxoethyl)carbamate

Participants

Reaction Steps

To a solution of 700 mg (4.34 mmol) of 2-(t-butoxycarbonylamino)ethanol in 35 mL of dry methylene chloride was added 4.8 mL (35 mmol) of triethylamine and 4.0 mL of dry dimethylsulfoxide. To the resulting solution was added in portions 2.8 g (17 mmol) of pyridine-sulfur trioxide complex. The resulting brown solution was s stirred at room temperature for 3 hours. The mixture was diluted with 500 mL of ether and transferred to a separatory funnel. The mixture was washed with 1N aqueous hydrochloric acid (2×50 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL). The organic layer was removed, dried over magnesium sulfate, filtered and the solvent removed under vacuum to afford 550 mg (80%) of the product as an oil. 1H NMR (200 MHz, CDCl3): δ1.42 (s, 9H), 4.04 (d, 4 Hz, 2H), 5.18 (s, 1H), 9.62 (s, 1H).

Provenance & Evidence