Sodium periodate → (R)-3,4-Dipropyl-1,2,3-oxathiazolidine 2,2-dioxide

Participants

Reaction Conditions

Reaction Steps

Ruthenium trichloride hydrate (10 mg) was added to a solution of (R)-3,4-dipropyl-1,2,3-oxathiazolidine 2-oxide (11.09 g) in ethyl acetate (58 mL) under stirring at 3° C. A cold saturated aqueous sodium periodate solution (200 mL) was added to the solution. The resulting suspension was stirred under ice-cooling for 10 minutes and then further stirred at room temperature for 1 hour. The suspension was filtered, and the insoluble matter was washed twice with ethyl acetate (15 mL). The filtrate and the washings were combined. The organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution (15 mL), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Tetrahydrofuran (13.5 mL) was added to the residue, and the mixture was concentrated under reduced pressure. The concentration was repeated three times. (R)-3,4-Dipropyl-1,2,3-oxathiazolidine 2,2-dioxide (11.22 g, 93% yield) was obtained as a brown oil.

Provenance & Evidence