Methyl Acrylate → 3-[(2-Methoxycarbonyl-ethyl)-methyl-amino]-butyric acid methyl ester

HRID 1827822Notes

Reaction equation

HRID 1827822 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

Reactant 2

HCID 7294Methyl AcrylateHCID 12636115Methyl 3-(methylamino)butanoate

Product 1

HCID 220914183-[(2-Methoxycarbonyl-ethyl)-methyl-amino]-butyric acid methyl esterYield 58%

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

  1. temperatureThe resulting solution was refluxed for 16 h
  2. temperatureThe reaction was cooled
  3. customan insoluble polymer separated out
  4. customThe hexane solution was decanted
  5. washthe polymer washed 2×100 mL hexanes with vigorous stirring
  6. concentrationThe combined hexane solutions were then concentrated in vacuo
  7. customThe crude product was purified by flash chromatography on SiO2 using pure CH2Cl2 as an eluent

Sources & evidence

ORD record
ord-e0737eca9ccd443d9ecf76b507cf523b
Source dataset
uspto-grants-2006_06
Patent number
US07056915B2

Reaction notes

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