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

Participants

Reaction Steps

To a solution of 1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-(trimethylsilyloxy)pyridine (20.4 g, 75.0 mmol) in CH3CN (500 mL) was added Selectfluor™ (29.2 g, 82.5 mmol) at room temperature, and the reaction mixture was stirred for 2 hr. EtOAc was added to the reaction mixture, and the mixture was washed with brine, dried over Na2SO4, and concentrated to dryness. Chromatography of the residue with CHCl3-MeOH (6:1, v/v) as eluent gave 1-tert-butoxycarbonyl-3-fluoro-4-piperidone (14.5 g, 89%) as a colorless oil. 1H-NMR (CDCl3) δ 1.50 (s, 9H), 2.44 (t, J=6.9 Hz, 1H), 2.48–2.63 (m, 2H), 3.26 (ddd, J=13.5, 10.5, 3.9 Hz, 1H), 3.72 (t, J=6.9 Hz, 1H), 4.16 (m, 1H), 4.42 (m, 1H), 4.83 (dt, 49.2, 6.9 Hz, 1H).

Provenance & Evidence