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

Participants

Reaction Conditions

Reaction Steps

To a 1.0 L flask was added tert-butyl 4-oxopiperidine-1-carboxylate (150.0 g, 752.8 mmol), which was dissolved in DMF (400 mL). To this solution was added TMS-Cl (114.7 mL, 903.4 mmol), followed by NEt3 (251.8 mL, 1807 mmol). The resulting heterogeneous mixture was warmed to 70° C. and stirred overnight under a N2 atmosphere. The mixture was cooled to ambient temperature, diluted with hexanes (250 mL) and filtered. The solids were washed with hexanes (4×250 mL). The combined organic phases were washed with a saturated aqueous NaHCO3 (3×250 mL) and brine (3×250 mL), dried over Na2SO4, and concentrated. The crude product was carried on directly to the next step.

Provenance & Evidence