Cyclopropylamine → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(hydroxymethyl)-4-(pyridin-2-yl)cyclohexanone (410 mg, 2.0 mmol, 1.0 equiv) in 1,2-dichloroethane (15 mL) was treated at 0° C. with cyclopropylamine (280 uL, 4.0 mmol, 2 equiv), acetic acid (0.1 mL) and NaBH(OAc)3 (848 mg, 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. The crude material was purified by flash column chromatography (SiO2, 5% MeOH/CH2Cl2 containing 2.5% NH4OH) to provide the trans amine. Further elution afforded the cis amine.

Provenance & Evidence