Methyl iodide → tert-Butyl 4-formyl-4-methylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 4-formylpiperidine-1-carboxylate (35.0 g, 164.1 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0° C. Potassium tert-butoxide (23.9 g, 213 mmol) was added followed by addition of iodomethane (69.9 g, 492 mmol). The reaction was stirred at 0° C. for 30 minutes, and then warmed to ambient temperature and stirred for 1.5 hr. The reaction mixture was poured into brine (400 mL) and the organic layer was separated, dried, and filtered, and concentrated and purified by silica gel to provide tert-butyl 4-formyl-4-methylpiperidine-1-carboxylate (16.36 g, 72.0 mmol, 43.8% yield).

Provenance & Evidence