(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 71014147, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(4-chloropyridin-2-yl)-4-hydroxypiperidine-1-carboxylate (C3) (0.600 g, 1.92 mmol) in CH2Cl2 (10 mL) cooled to −78° C. was added bis(2-methyoxyethyl)aminosulfur trifluoride (Deoxofluor, 0.71 mL, 3.8 mmol). The reaction was slowly warmed to −40° C. over 3 h, then quenched with water (5 mL) and warmed to RT. The mixture was extracted with CH2Cl2 (2×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was purified via silica gel chromatography eluting with 10-40% ethyl acetate in hexanes to provide tert-butyl 4-(4-chloropyridin-2-yl)-4-fluoropiperidine-1-carboxylate (C4).

Provenance & Evidence