Selectfluor → TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.5 g, 1.84 mmol) in dry acetonitrile (5.0 mL) was added SelectFluor (0.654 g, 1.84 mmol), and the reaction mixture was stirred for 75 minutes. At this time, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with brine (50 mL), dried over anhyd. Na2SO4 and concentrated under vacuum to give the title compound (0.25 g, 62%) which was used as obtained for the next transformation. LCMS (Condition D): m/z 218.2 +ve with retention time=1.51 min. 1H-NMR (400 MHz, CDCl3) δ ppm: 4.30-4.42 (m, 1H), 3.72-3.84 (m, 1H), 3.42-3.58 (m, 3H), 1.93-1.97 (m, 1H), 1.70-1.74 (m, 1H), 1.46 (s, 9H). 19F-NMR (400 MHz in CDCl3): δ ppm: −203.24 (1F).

Provenance & Evidence