Ethyl Acetate → HCID 57541275, compound

Participants

Reaction Steps

Potassium tert-butoxide (1.22 g, 10.8 mmol) were added to tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate (2.11 g, 9.85 mmol) in DMF (10 mL) at 0° C. under argon. The resulting suspension was stirred for 20 mins. 2-Fluoropyridine (0.85 mL, 9.85 mmol) was added to the reaction mixture and the resulting solution was stirred at 80° C. for 21 hours. The reaction mixture was poured into ice water (100 mL) and extracted with EtOAc (2×50 mL). The organic layers were combined and washed with brine (2×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. Flash column chromatography (silica, gradient 5 to 100% EtOAc in isohexane) yielded tert-butyl 4-oxo-3-(2-oxo-1,2-dihydropyridin-3-yl)piperidine-1-carboxylate (0.654 g, 23%) as a cream solid.

Provenance & Evidence