Water → HCID 13079622, compound

Participants

Reaction Steps

To a slurry of lithium aluminium hydride (200 mg) in dry tetrahydrofuran (20 ml) was added dropwise, with stirring, a solution of N-[2-(4-(3-carbomethoxypropoxy)phenyl)-1-methylethyl)-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (800 mg) in dry tetrahydrofuran (30 ml). The mixture was stirred and heated under reflux for 2 hours after which time it was cooled in ice. Water (0.2 ml), 2 M sodium hydroxide (0.2 ml) and water (1 ml) were successively added, the resulting mixture filtered, the tetrahydrofuran dried (magnesium sulphate) and evaporated to leave an oil. Crystallisation from hexane gave N-[2-(4-(4-hydroxybutoxy)phenyl)-1-methylethyl]-2-hydroxy-2-(3-trifluoromethylphenyl)ethanamine (450 mg) m.p. 69°-76° as a 45:55 mixture of diastereoisomers.

Provenance & Evidence