Tetrabutylammonium Fluoride → Tetrabutylammonium Fluoride

Participants

Reaction Conditions

Reaction Steps

[Trans-4-(tert-butyl-dimethyl-silyloxy)-cyclohexyl]-(4-trifluoromethylsulfanyl-phenyl)-amine (180 mg, 0.44 mmol, prepared in accordance with Example 28) was dissolved in tetrahydrofuran (3 mL). A molar solution of tetrabutylammonium fluoride (500 μL, 5 mmol) was then added. The resulting mixture was heated to 40° C. and then maintained at that temperature for 4 hr. After cooling to room temperature, the mixture was diluted with diethylether (20 mL), washed with water (10 mL), and washed with saturated aqueous hydrogencarbonate (10 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The oily residue obtained was purified by column chromatography on silica gel (dichloromethane and then dichloromethane/methanol, 95:5). The desired product was isolated as a colorless oil with traces of tetrabutylammonium fluoride.

Provenance & Evidence