Sodium Hydroxide → (1RS,2SR)-2-amino-3-[3-(tert-butyl)phenyl]-1-(3-chlorophenyl)-1-propanol

Participants

Reaction Steps

To a solution of (4RS,5SR)-4-[3-(tert-butyl)benzyl]-5-(3-chlorophenyl)-1,3-oxazolidin-2-one (2.36 g, 6.86 mmol) in ethanol (60 ml) was added 8N aqueous sodium hydroxide (4.3 ml, 34.3 mmol), and the mixture was heated under reflux for 5 hrs. After the completion of the reaction, ethanol was evaporated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization (hexane-ethyl acetate) to give (1RS,2SR)-2-amino-3-[3-(tert-butyl)phenyl]-1-(3-chlorophenyl)-1-propanol (1.21 g, 55%) as colorless crystals.

Provenance & Evidence