Acetic Acid → (1R,2S)-Tranylcypromine

Participants

Reaction Conditions

Reaction Steps

Cyclopropyl amine (12.4 mL, 185 mmol) was added to a solution of the ketone prepared above (27.0 g, 123 mmol) in dichloroethane (600 mL) and acetic acid (14.0 mL, 246 mmol). The reaction mixture was cooled to 0° C. and NaBH(OAc)3 (52 g, 246 mmol) was added protionwise. After being stirred for 2.75 h at 23° C., the reaction was re-cooled to 0° C. and quenched with 1 M NaOH (200 mL). The aqueous layer was extracted with CH2Cl2 (2×200 mL) and the combined organic layers were washed with brine (300 mL), dried with MgSO4, filtered, and concentrated in vacuo. The crude mixture of cis and trans amines was purified by flash column chromatography 75% EtOAc/hexanes (2.5% TEA)→100% EtOAc (2.5% TEA)→10% MeOH/CH2Cl2 (1% NH4OH) to provide the trans amine as an off-white solid.

Provenance & Evidence