Ethyl Acetate → Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-(trimethylsilyloxy)pyridine (400 g, 14.7 mmol) in anhydrous acetonitrile (160 mL) under nitrogen was added Selectfluor™ reagent (5.74 g, 16.2 mmol) and the mixture was stirred for 75 min. The mixture was poured into ethyl acetate (600 mL), washed with diluted brine (300 mL), then saturated NaCl solution (100 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (alumina, 0-5% MeOH/EtOAc) to afford 2.91 g (91%) of the title compound as a colourless oil. δH (250 MHz, CDCl3) 1.50 (9H, s), 2.52-2.64 (2H, m), 3.22-3.38 (2H, m), 4.18 (1H, m), 4.45 (1H, m), 4.83 (1H, m).

Provenance & Evidence