Tranylcypromine → 4-(2-Phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

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Reaction Steps

To a stirred solution of cis-N-(benzyloxycarbonyl)-4-carboxy-proline methyl ester (615 mg, 2 mmol) and HOSu (173 mg, 3 mmol) in 1,4-dioxane (2 mL) was added a solution of DCC (454 mg, 2.2 mmol) in CH2Cl2 (2 mL). After 10 min at room temperature, 2-phenylcyclopropylamine (266 mg, 2 mmol) in CH2Cl2 (1 mL) was added with stirring. After 16 h, the resulting N,N′-dicyclohexylurea was removed by filtration. The filtrate was washed with saturated aqueous NaHCO3 (5 mL), 1 N aqueous citric acid (5 mL), water (5 mL), dried over MgSO4 and concentrated. The residue was purified by a silica gel column using hexane/EtOAc (6:4) as eluant to yield the desired compound as a colorless oil (633 mg, 75%).

Provenance & Evidence