Acetic Acid → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(hydroxymethyl)-4-phenylcyclohexanone (5.0 g, 24.5 mmol, 1.0 equiv.) in 1,2-dichloroethane (50 mL) was treated at 0° C. with cyclopropylamine (4.2 g, 74.0 mmol, 3.0 equiv.), 1 mL acetic acid and NaBH(OAc)3 (15.6 g, 74.0 mmol, 3.0 equiv.) successively. After being stirred at 25° C. for 12 h, the reaction mixture was diluted (EtOAc), washed (1×1 N aqueous NaOH and 2× brine), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 50% EtOAc/n-Hexane with 5% TEA) gave the trans amine isomer (the bottom spot on the TLC).

Provenance & Evidence