1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(Allyl-benzyl-carbamoyl)-but-3-enoic acid methyl ester

Participants

Reaction Steps

587 mg of 2-methylene-succinate 4-methyl ester (4.07 mmol), 781 mg of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (4.07 mmol) and 75 mg of 4-(dimethylamino)pyridine (0.61 mmol) were added to the reaction solution containing 300 mg of allylbenzylamine (2.04 mmol) dissolved in methylene chloride solution (0.5 M) with stirring for 10 hrs at room temperature. After the resulting mixture was washed with 5% HCl solution (10 ml), the mixture was diluted with ethyl acetate, washed with 10 ml of solution mixture mixed with saturated NaHCO3 solution and saturated NaCl solution to separate into an organic layer and water layer. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with EtOAc and hexanes (1:1) as an eluant to give 272 mg of 3-(allyl-benzyl-carbamoyl)-but-3-enoic acid methyl ester (o) (yield: 49%).

Provenance & Evidence