4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinebutanoic acid ethyl ester → HCID 15042243, compound

Participants

Reaction Steps

A solution of 15.4 g (0.037 mol) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinebutanoic acid ethyl ester in 100 mL of dry (freshly distilled from lithium aluminum hydride) tetrahydrofuran was added dropwise to a mixture of 3.5 g (0.092 mol) of lithium aluminum hydride in 100 mL of dry tetrahydrofuran. After the final addition, the mixture was stirred at ambient temperature for 3 h, whereupon the excess lithium aluminum hydride was quenched by successive dropwise additions of 4 mL of water, 4 mL of 15% sodium hydroxide solution and 12 mL of water. The mixture was stirred for 30 min, filtered, and the filtrate concentrated under reduced pressure to yield 11.2 g (100%) of an oil which crystallized upon standing. A portion of the solid was recrystallized from ethyl acetate/petroleum ether (30°-60° C.) to give the title compound as a light-tan solid, mp 130°-131° C.

Provenance & Evidence