4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester → HCID 67928225, compound

Participants

Reaction Steps

A solution of 16.8 g (0.040 mol) of 4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinepentanoic acid ethyl ester in 100 mL of dry (freshly distilled from lithium aluminum hydride) tetrahydrofuran was added dropwise to a solution of 3.8 g (0.100 mol) of lithium aluminum hydride in 100 mL of dry tetrahydrofuran while stirring vigorously at ambient temperature for 1 h and the excess lithium aluminum hydride was quenched by successive, dropwise additions of 4 mL of water, 4 mL of a 15% sodium hydroxide solution, and 12 mL of water. The solution was allowed to stir for 30 min, filtered, and the filtrate concentrated under reduced pressure to yield 11.5 g (98%) of an off-white solid. A portion of the solid was recrystallized from ethyl acetate/petroleum ether (30°-60° C.) to give the title compound as a white solid, mp 103°-105° C.

Provenance & Evidence