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

Temperature

3 °C

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.

1. stirringThe resulting suspension was stirred under ice-
2. temperaturecooling for 10 minutes
3. stirringfurther stirred at room temperature for 1 hour
4. filtrationThe suspension was filtered
5. washthe insoluble matter was washed twice with ethyl acetate (15 mL)
6. customThe organic layer was separated
7. washwashed with a saturated aqueous sodium hydrogen carbonate solution (15 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. additionTetrahydrofuran (13.5 mL) was added to the residue
11. concentrationthe mixture was concentrated under reduced pressure
12. concentrationThe concentration

ORD record

ord-ae8bda60416a42a392797c7524266f82

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807840B2