Reaktion #69358

Reaktionsgleichung

2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione

4-(4-aminophenyl)-3-morpholinone

2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione

→

2-((2R)-2-Hydroxy-3-{[4-(3-oxo-4-morpholinyl)phenyl]amino}propyl)-1H-isoindole-1,3(2H)-dione

Lösungsmittel

ethanol water

ethanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONdissolves
2. 2
   FiltrationThe precipitate (desired product) is filtered off
3. 3
   Waschenwashed three times with diethyl ether
4. 4
   Sonstigedried
5. 5
   EinengenThe combined mother liquors are concentrated under reduced pressure
6. 6
   Temperaturrefluxed for 13 h (the precipitate
7. 7
   workup.DISSOLUTIONdissolves
8. 8
   FiltrationThe precipitate (desired product) is filtered off
9. 9
   Waschenwashed three times with diethyl ether
10. 10
    Sonstigedried

Vorschrift

A suspension of 2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione (A. Gutcait et al. Tetrahedron Asym. 1996, 7, 1641) (5.68 g, 27.9 mmol) and 4-(4-aminophenyl)-3-morpholinone (5.37 g, 27.9 mmol) in ethanol/water (9:1, 140 ml) is refluxed for 14 h (the precipitate dissolves, after some time again formation of a precipitate). The precipitate (desired product) is filtered off, washed three times with diethyl ether and dried. The combined mother liquors are concentrated under reduced pressure and, after addition of a second portion of 2-[(2S)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione (2.84 g, 14.0 mmol), suspended in ethanol/water (9:1, 70 ml) and refluxed for 13 h (the precipitate dissolves, after some time again formation of a precipitate). The precipitate (desired product) is filtered off, washed three times with diethyl ether and dried. Total yield: 10.14 g, 92% of theory.

Quelle