Hydrochloric Acid → Tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

Participants

Reaction Steps

To a solution of tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2-oxide in acetonitrile (50 mL) and water (30 mL) cooled to 0° C. is added sodium periodate (6.4 g, 30.0 mmol). After 5 min, the pH of the mixture is adjusted to 7-8 by addition of saturated Na2HPO4 solution. Then the solution of RuCl3 (41.5 mg, 0.2 mmol) in water (0.5 mL) is added. The pH of the reaction mixture is kept between 6 and 9 by addition of Na2HPO4 solution. After stirring for 2 h, water (100 mL) is added and the pH is adjusted to 6 by addition of 2 M HCl solution. The mixture is extracted with EtOAc and the organic layer is separated, washed with NaHCO3 and brine. The aqueous washing layers are back extracted once with EtOAc. The combined organic layers are dried (MgSO4) and concentrated to afford the crude compound which is purified by flash column chromatography using EtOAc in hexanes to afford the title compound (4.48 g, 85% for 4 steps).

Provenance & Evidence