Reacción #1379897

ord-40560b34d0344e9a881657df5ce95af3

Ecuación de reacción

NCCNCCO
2-(2-aminoethylamino)ethanol
C=CC(=O)OCc1ccccc1
benzyl acrylate
NCCNC(CO)CCC(=O)OCc1ccccc1
2-(benzyloxycarbonylethyl]-2-(2aminoethylamino)ethanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawas heated
  2. 2
    Temperaturaat reflux for 24 hours
  3. 3
    OtroThe excess reagent was removed under reduced pressure
  4. 4
    Otrothe resulting oil was purified by flash chromatography
  5. 5
    workup.ADDITIONa mixture of dichloromethane and ethyl acetate (60:40)
  6. 6
    Lavadoto elute the desired material
  7. 7
    OtroFractions were collected

Procedimiento

A solution of 2-(2-aminoethylamino)ethanol (4.6648 g; 44.8 mmole) dissolved in 35 mL of benzyl acrylate was heated at reflux for 24 hours. The excess reagent was removed under reduced pressure and the resulting oil was purified by flash chromatography using a mixture of dichloromethane and ethyl acetate (60:40) to elute the desired material. Fractions were collected and analyzed to determine which of these contain the product. Solvents were eliminated under vacuum to give 5.8 g (21.9%) of N,N,N′-tris[2-(benzyloxycarbonylethyl]-2-(2aminoethylamino)ethanol (8).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07238339B2uspto-grants-2007_07