Water → HCID 23036274, compound

Participants

Reaction Steps

To a stirred slurry of 7.6 g (0.02 mole) of lithium aluminum hydride in 150 ml of freshly distilled tetrahydrofuran was added dropwise, over a 45 min period, a solution of 38.5 g (0.098 mole) of 4-[bis(4-fluorophenyl)hydroxymethyl-1-(phenylmethyl)-2-pyrrolidinone in 150 ml of tetrahydrofuran. After the addition was complete, the mixture was heated at reflux for 2 hr and then let stir at ambient temperature overnight. The excess lithium aluminum hydride was decomposed by the successive addition of 8 ml of water, 8 ml of a 15% sodium hydroxide solution, and 24 ml of water. The mixture was stirred for 30 min and filtered. The filtrate was concentrated under reduced pressure and the residue crystallized when triturated with petroleum ether (30°-60° C.). The solid was collected by filtration and recrystallized from 2-propanol to yield 30.3 g (81%) of the title compound as a white solid, mp 99°-100° C.

Provenance & Evidence