Cyclopropylamine → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-oxo-1-(pyrazin-2-yl)cyclohexyl)propanenitrile (610 mg, 2.7 mmol, 1.0 equiv) in acetonitrile (10 mL) was treated with cyclopropylamine (380 μL, 5.3 mmol, 2.0 equiv), acetic acid (0.1 mL) and NaBH(OAc)3 (1.1 g, 5.3 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 with brine, dried with Na2SO4 and concentrated under reduced pressure. Purification of the crude material by flash chromatography (SiO2, 70-80% EtOAc/hexanes containing 2.5% triethylamine) gave 0.24 g of the trans amine (0.89 mmol, 33%) and then further elution afforded 0.24 g of the cis amine (0.89 mmol, 33%).

Provenance & Evidence