Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (1.0 g, 5 mmol) in dry DMF (5 mL) under argon was added triethylamine (1.67 mL, 12 mmol) followed by TMSCl (0.95 mL, 7.5 mmol), and the reaction mixture was stirred at 80° C. for 16 h under argon. The reaction mixture was diluted with hexane (10 mL) and washed with cold saturated sodium bicarbonate (3×10 mL). The organic layer was dried over anhyd. Na2SO4 and concentrated under vacuum. The crude product obtained was purified by flash chromatography to give the title compound as a colorless oil (1.2 g, 88%). LCMS (Condition D): m/z 272 +ve with retention time=2.18 min. 1H-NMR (400 MHz, CDCl3): δ ppm: 4.80 (s, 1H), 3.88 (bs, 1H), 3.52-3.55 (t, J=6 Hz, 2H), 2.11 (bs, 2H), 1.47 (s, 9H), 0.20 (s, 9H).

Provenance & Evidence