Sodium Hydroxide → (1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine

Participants

Reaction Steps

(4RS,5SR)-5-(4-Fluorophenyl)-4-[4-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (18.75 g, 55.26 mmol) and sodium hydroxide (8.84 g, 221 mmol) were heated under reflux in ethanol (100 ml)-water (10 ml) for 5 hrs. The reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic-layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=1/1-ethyl acetate) and crystallized from diethyl ether-hexane to give the objective substance.

Provenance & Evidence