Methyl iodide → HCID 22730047, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion on mineral oil) (198 mg, 4.95 mmol) was added portionwise to tert-butyl 4-hydroxy-4-methylpiperidine-1-carboxylate (21) (710 mg, 3.30 mmol) in N,N-dimethylformamide (12 mL) at ambient temperature over a period of 30 seconds under an air atmosphere. The resulting suspension was stirred at 25° C. for 20 minutes. Methyl iodide (0.411 mL, 6.60 mmol) was then and the resulting suspension was stirred at 25° C. for 18 hours. The reaction mixture was diluted with water (150 mL) and saturated brine (25 mL), then washed sequentially with dichloromethane (3×100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product, which was used directly in the next stage.

Provenance & Evidence