Tetrahydrofuran → HCID 23194322, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-cyanopiperidine-1-carboxylate (0.220 g, 1.05 mmol) and 2-fluoro-4-methylpyridine (0.107 g, 1.10 mmol, 1.05 equiv) were suspended in THF (5 mL), cooled to 78° C., and treated with sodium bis(trimethylsilyl)amide (1 M solution in diethyl ether, 1.47 mL, 1.47 mmol, 1.40 equiv) dropwise. After 1 hour, the mixture was warmed to ambient temperature, treated with saturated aqueous ammonium chloride, and extracted with dichloromethane (3×). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (100:0 to 4:1 hexanes:ethyl acetate), providing Cert-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate. The resulting clear oil was suspended in ethyl acetate (5 mL), cooled to 0° C. and saturated with gaseous hydrogen chloride. The mixture was warmed to ambient temperature and after 18 hours, was concentrated in vacuo, providing the titled compound.

Provenance & Evidence