Sodium hydride → Dimethyl 2,3-dihydro-1H-pyrrolizine-1,7-dicarboxylate
Reaction equation
I[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]1[CH2:13][C:14]([O:16][CH3:17])=[O:15].[H-].[Na+]>CN(C)C=O>[CH:13]1([C:14]([O:16][CH3:17])=[O:15])[CH2:2][CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[C:5]12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1 g of methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate in 5 ml of dry dimethylformamide is stirred, under an atmosphere of argon, with 137 mg of 50% sodium hydride in mineral oil. The reaction mixture is maintained for 20 minutes at room temperature and then quenched with 100 ml of water. The product is extracted with ethyl acetate (3×50 ml), the combined extracts are washed with water, dried over magnesium sulfate and evaporated to dryness. Chromatography of the residue on 20 g of silica gel using hexane:ethyl acetate (4:1) as eluant, affords 500 mg (80%) of dimethyl 1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1,7-dicarboxylate (VII, R=H) m.p. 70°-71° C.