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

Participants

Reaction Conditions

Reaction Steps

To a solution of t-butyl 4-oxopiperidine-1-carboxylate (52.6 g, 264 mmol) in anhydrous DMF (140 mL) was added TMSCl (40.2 mL, 317 mmol) followed by triethylamine (88.3 mL, 634 mmol). The resulting heterogeneous mixture was warmed to 80° C. and stirred for 16 hours. The cooled mixture was diluted with hexanes (500 mL), washed with saturated NaHCO3 (3×300 mL) and brine (200 mL), then dried over Na2SO4, filtered and concentrated to afford 68 g (95%) of desired product as an oil.

Provenance & Evidence