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

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Reaction Steps

To a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.0 mmol) in anhydrous DMF (50 mL), trimethylsilyl chloride (3 mL, 30.1 mmol) and triethylamine (8.3 mL, 60.2 mmol) were added at 80° C. and stirred for 10-12 h. The reaction mixture was cooled to room temperature, diluted with hexane and washed with saturated NaHCO3. Combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate as a pale yellow oil (2.16 g, 32%); MS: 271 (M+).

Provenance & Evidence