Diethyl Ether → HCID 19097374, compound

Participants

Reaction Steps

Methyl iodide (138.4 g, 0.98 mole) was added dropwise over 1.5 hours to magnesium turnings (23.7 g, 0.98 mole) in ether (300 mL). The solution was diluted to a total volume of 1 liter and was stirred at room temperature for 2 hours. The solution was filtered through a glass wool plug into a second flask under nitrogen and a solution of ethyl 3,4,8-trimethyl-2-(phenylmethyl)-2-azabicyclo[2.2.21-octane-6-carboxylate (87.9 g, 0.28 mole) in ether (400 mL) was added over 2 hours. The mixture was stirred at room temperature for 1 hour, poured into a mixture of saturated NH4Cl (100 mL) and ice-water (100 mL) and the organic layer was separated. The aqueous phase was extracted with ether (2×700 mL) and the combined organic layers were washed with water (2×500 mL) , then brine (500 mL) and were dried over anhydrous MgSO4. The solvent was removed in vacuo to afford 82.5 g (98%) of α,α,3,4,8-pentamethyl-2-(phenylmethyl)-2-azabicyclo[2.2.21octane-6-methanol.

Provenance & Evidence