Methyl iodide → Tert-butyl 4-methoxypiperidine-1-carboxylate

Participants

Reaction Steps

Sodium hydride (1.19 g, 60% in mineral oil, 29.7 mmol) was added portionwise to a cooled (10° C.) solution of tert-butyl 4-hydroxy-1-piperidinecarboxylate (Bioorg. Med. Chem. Lett. 10; 24; 2000; 2815) in tetrahydrofuran (80 mL), and the suspension stirred at room temperature for 1 hour. Iodomethane (1.85 mL, 29.7 mmol) was added, and the reaction stirred at 50° C. for 20 hours. The mixture was diluted with water (50 mL), extracted with ethyl acetate (2×150 mL) and the combined organic extracts washed with saturated sodium bicarbonate solution (50 mL), dried (MgSO4) and evaporated under reduced pressure, to afford the title compound as a golden oil, 5.24 g.

Provenance & Evidence