Sodium Hydroxide → (1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol

Participants

Reaction Steps

To a solution of (4RS,5SR)-5-(4-phenoxyphenyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidin-2-one (6.0 g, 14.5 mmol) in ethanol (100 ml) was added 8N aqueous sodium hydroxide solution (9.0 ml, 72 mmol), and the mixture was heated under reflux for 4 hrs. The reaction solution was concentrated, diluted with water (300 ml) and extracted with ethyl acetate (300 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give (1RS,2SR)-2-amino-1-(4-phenoxyphenyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (4.21 g, 75%) as a colorless oil. A portion thereof was recrystallized from ethanol-ether as hydrochloride, which was measured for elemental analysis values.

Provenance & Evidence