Acetic Acid → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

A solution of product obtained above (20 g, 89.7 mmol, 1.0 equiv.) in CH3CN (200 mL) was treated at 0° C. with cyclopropylamine (10.24 g, 179.4 mmol, 2.0 equiv), acetic acid (2 mL) and NaBH(OAc)3 (38 g, 179.4 mmol, 2.0 equiv) successively. After being stirred at 25° C. for 12 h, the reaction mixture was carefully diluted (sat.NaHCO3) and extracted (10% MeOH/CH2Cl2). The organics were washed (brine), dried (Na2SO4) and concentrated under reduced pressure to give the crude mixture of cis and trans amines. The mixture was separated by flash chromatography (SiO2) using 60% EtOAc/hexanes with 2.5% TEA to get rid of the undesired isomer (top spot). Further elution using 5% MeOH/DCM with 2.5% TEA gave 12.5 g of the trans amine as white solid.

Provenance & Evidence