(-)-Mandelic acid → (1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine

Participants

Reaction Steps

R-(−)-Mandelic acid (22.2 g, 0.14 mol) was added to a solution of (trans)-2-(4-(benzyloxy)phenyl)cyclopropanamine hydrochloride (intermediate V) (35 g, 0.14 mol) in a mixture of THF and H2O (6:4) (650 mL) and refluxed for 1 h. After formation of a clear solution the reaction mixture was cooled to RT. The solid precipitated formed was filtered, basified with sat. NaHCO3 solution and extracted with ethyl acetate (3×500 mL). The combined organic extracts were washed with water (500 mL), brine (500 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to afford trans 2-(4-(benzyloxy)phenyl)cyclopropanamine (enantiomer-(−)) (14 g, 46.6%) as an off white solid.

Provenance & Evidence