反应详情

To 4-fluoro-N-[(1R)-3-hydroxy-1-(hydroxymethyl)propyl]benzenesulfonamide (35.0 g, 133 mmol) in THF (700 mL) was added 1,1′-(azodicarbonyl)dipepiridine (35.0 g, 139 mmol, 1.04 equiv.) followed by tributylphosphine (28.7 g, 142 mmol, 1.07 equiv.) over 10 min. After a period of 2 h, the reaction mixture was filtered and the solid washed with methyl tert-butyl ether (100 mL). Water (200 mL) was added to the filtrate and the organic phase was separated which in turn was washed with 100 mL of 3% hydrogen peroxide. The organic phase was then washed with water and half-saturated sodium chloride. The organic phase was collected, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was treated with methyl tert-butyl ether and the mixture filtered. The filtrate was evaporated and purified by flash chromatography with 50% ethyl acetate to 70% ethyl acetate in hexane to provide 31 g of the title compound.

1. filtrationthe reaction mixture was filtered
2. washthe solid washed with methyl tert-butyl ether (100 mL)
3. additionWater (200 mL) was added to the filtrate
4. customthe organic phase was separated which in turn
5. washwas washed with 100 mL of 3% hydrogen peroxide
6. washThe organic phase was then washed with water and half-saturated sodium chloride
7. customThe organic phase was collected
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customevaporated under reduced pressure
11. additionThe residue was treated with methyl tert-butyl ether
12. filtrationthe mixture filtered
13. customThe filtrate was evaporated
14. custompurified by flash chromatography with 50% ethyl acetate to 70% ethyl acetate in hexane