Ethanolamine → HCID 57487387, Verbindung

HRID 348994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348994
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:7][C:6]1=O)[CH2:2][CH2:3][CH3:4].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.C(CN)O>O1CCCC1>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[N:8]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 57487386HCID 57487386, Verbindung

Produkt 1

HCID 57487387HCID 57487387, VerbindungAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-tert-butyl 6-methyl 4-butyl-3-oxo-3,4-dihydroquinoxaline-1,6(2H)-dicarboxylate (440 mg) and 9-BBN dimer (600 mg) in tetrahydrofuran (10 mL) was heated at 65° C. for 10 h. The mixture was cooled to room temperature, ethanolamine (0.15 mL) was added and the resulting solution was concentrated under reduced pressure. The residue was washed with hexanes, filtered, and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) afforded 158 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.50, 7.34, 7.28, 3.88, 3.77, 3.38–3.30, 1.65–1.51, 1.42–1.34, 0.99–0.94.

Aufarbeitung

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. washThe residue was washed with hexanes
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-13799ebfe1e5413da95fb287b027cf6d
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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