Réaction #59655

Équation de réaction

2-phenylcyclopropylamine

cis-N-(benzyloxycarbonyl)-4-carboxy-proline methyl ester

HOSu

DCC

→

desired compound

Rendement 75.0%

4-(2-phenyl-cyclopropylcarbamoyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Rendement 75.0%

Solvants

CH2Cl2

1,4-dioxane

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 16 h
2. 2
   Autrethe resulting N,N′-dicyclohexylurea was removed by filtration
3. 3
   LavageThe filtrate was washed with saturated aqueous NaHCO3 (5 mL), 1 N aqueous citric acid (5 mL), water (5 mL)
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   AutreThe residue was purified by a silica gel column

Mode opératoire

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%).

Source