1,2-Dichloroethane → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

A solution of trans-4-(cyclopropylamino)-1-(2-fluorophenyl)cyclohexanecarbonitrile (4.4 g, 20.2 mmol, 1.0 equiv.) in 1,2-dichloroethane (40 mL) was treated at 0° C. with cyclopropylamine (2.31 g, 40.4 mmol, 2.0 equiv.) and NaBH(OAc)3 (8.56 g, 40.4 mmol, 2.0 equiv.) successively. After being stirred at 25° C. for 12 h, the reaction mixture was diluted (EtOAc), washed (1×1 N NaOH and 2× brine), dried (Na2SO4) and concentrated under reduced pressure. Purification by flash chromatography (SiO2, 20% EtOAc/n-Hexane containing 2.5% of TEA) gave the trans amine as a colorless oil.

Provenance & Evidence