Methyl iodide → HCID 54235817, compound

Participants

Reaction Steps

DMF 3 ml solution of trans-(1S)-3-[2-(5-hydroxy-2-adamantyl)ethyl]-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane (compound No. 58,8) 113 mg was added in a DMF suspension 2.5 ml of sodium hydride (60%, oil dispersion) 41.0 mg at 0° C., and after changing the temperature to room temperature, the reaction mixture was stirred for 1.1 hour. Methyl iodide 70 gI was added to the reaction mixture and stirred at the same temperature for 20 hours. The reaction mixture was cooled to O@C, aqueous saturated ammonium chloride and water were added in this order, then extracted with chloroform. Organic layer was separated and solvent was distilled off in vacuo. Residue was purified by means of silica gel column chromatography to obtain trans (IS)-3-[2-(5-methoxy-2-adamantyl)ethyl]-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. Yield: 33. gmg (Yield 29%).

Provenance & Evidence