Tetrabutylammonium Fluoride → HCID 72574147, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethoxy)-3-fluorocyclohexylcarbamate (5.83 g, 12.5 mmol) in THF (100 mL) was added tetrabutylammonium fluoride (25 mL, 25 mmol, 1M in THF) and the reaction mixture was stirred at room temperature for 8 h. The mixture was extracted with ethyl acetate (4×), and the combined organics washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (hexane: ethyl acetate 80:20 then 60:40) gave tert-Butyl 3-fluoro-4-(2-hydroxy-2-phenylethoxy)cyclohexylcarbamate (4.33 g) as a white solid.

Provenance & Evidence