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

HRID 915223Notes

Reaction equation

HRID 915223 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-ca2c9fb4a0ea43f79f9866952ce0b3d7
Source dataset
uspto-grants-2007_09
Patent number
US07265132B2

Reaction notes

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