Tributylphosphine → 2-{(2R)-1-[(4-Fluorophenyl)sulfonyl]aziridin-2-yl}ethanol

Participants

Reaction Steps

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.

Provenance & Evidence