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

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-oxopiperidine-1-carboxylate (10 g, 48.7 mmol) was dissolved in dry DMF (12.0 mL). Trimethylsilyl chloride (6.35 g, 7.39 mL, 58.4 mmol) and triethylamine (11.8 g, 16.2 mL, 117 mmol) were added under argon and the reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, saturated NaHCO3 solution was added and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (1 drop Et3N was added during conditioning of the column) (silica gel, 100 g, 0% to 100% pentane in Et2O, 45 minutes). The title compound was obtained as a colorless liquid (13.2 g, 99%).

Provenance & Evidence