HCID 19097385, compound → HCID 19738112, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2,3,4,8-tetramethyl-2-azabicyclo-[2.2.2]octane-6-carboxylate (18.3 g, 76.5 mmol) in ether (200 mL) was added to a slurry of lithium aluminum hydride (5.8 g, 153 mmol) in ether (60 mL). The mixture was stirred for 1 hour, cooled to 0° C. and quenched by the sequential addition of water (5.8 mL), 15% NaOH (5.8 mL), and water (17.4 mL). The aluminum salts were removed by filtration and the filtrate was concentrated in vacuo to afford 14.8 g (98%) of 2,3,4,8-tetramethyl-2-azabicyclo[2.2.2]octane-6-methanol as a colorless oil. The product was dissolved in ether and treated with 4.9N ethereal.HCl to afford 9.1 g of the hydrochloride salt as a white solid, m.p. 158°-159° C.

Provenance & Evidence