Methyl Acrylate → 3-[(2-Methoxycarbonyl-ethyl)-methyl-amino]-butyric acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH:5]([NH:7][CH3:8])[CH3:6].[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12]>>[CH3:1][O:2][C:3](=[O:9])[CH2:4][CH:5]([N:7]([CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13])[CH3:8])[CH3:6]Participants
3
Procedure
3-Methylamino-butyric acid methyl ester (7.6 g, 58 mmol, 1.0 equiv) was added neat to methyl acrylate (7.5 g, 87 mmol, 1.5 equiv). The resulting solution was refluxed for 16 h. The reaction was cooled and diluted with hexanes (200 mL) and an insoluble polymer separated out. The hexane solution was decanted and the polymer washed 2×100 mL hexanes with vigorous stirring. The combined hexane solutions were then concentrated in vacuo. The crude product was purified by flash chromatography on SiO2 using pure CH2Cl2 as an eluent. The pure product was isolated as a clear colorless oil (7.3 g, 58%); MS, m/z 218=M+1.
Workup
- temperature