Triethylamine → HCID 86670531, compound

Participants

Reaction Conditions

Reaction Steps

To a tetrahydrofuran (20 mL) solution of the trifluoroacetate salt of piperidin-4-yl 4-(trifluoromethyl)benzenesulfonate (800 mg, 1.97 mmol) at −78° C. was added tert-butylsulfinyl chloride (209 μL, 2.20 mmol). The reaction mixture was stirred for 10 minutes at −78° C. before triethylamine (1.10 mL, 7.88 mmol) was added. It was then stirred for another 2 hours at −78° C. Diethyl ether (50 mL) was added to the reaction mixture, and the combined organic layers were washed with 1 M hydrochloric acid (30 mL), water (30 mL), brine (30 mL), dried (sodium sulfate), filtered and concentrated in vacuo. The resulting oil was dissolved in dichloromethane (20 mL), cooled to 0° C., and m-chloroperbenzoic acid (374 mg, 2.17 mmol) was added to the solution. The ice-bath was removed, and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was washed with saturated sodium bicarbonate (40 mL), water (40 mL), brine (40 mL), dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound.

Provenance & Evidence