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[2.2.2]-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 (700 mL) and ice-water (1000 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%) α,α,3,4,8-pentamethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]octane-6-methanol. A small portion of the product (5.0 g) was treated with ethereal HCl to afford the hydrochloride salt as a white solid, m.p. 221°-222° C. (dec) when recrystallized from ethanol/ether.

Provenance & Evidence