Water → HCID 18706355, Verbindung

HRID 1422219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422219
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]2[C:6]=1[NH:7][CH:8]([O:18][CH3:19])[CH:9]([O:16][CH3:17])[NH:10]2)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]2[C:6]=1[NH:7][CH:8]([O:18][CH3:19])[CH:9]([O:16][CH3:17])[NH:10]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18706342HCID 18706342, Verbindung

Produkt 1

HCID 18706355HCID 18706355, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

4.47 g (13.8 mmol) of 5-azidomethyl-7-bromo-2,3-dimethoxy-1,2,3,4-tetrahydroquinoxaline are dissolved in 35 ml of tetrahydrofuran, and 3.98 g (1.1 equiv.) of triphenylphosphine are added. The mixture is stirred at 20° C. for 4 hours. 746 mg of water are added and the mixture is stirred for a further three hours. The solid is filtered off and the filtrate is extracted with ethyl acetate and sodium carbonate solution. The organic phases are combined, washed with brine, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/petroleum ether (1:1).

Aufarbeitung

  1. stirringthe mixture is stirred for a further three hours
  2. filtrationThe solid is filtered off
  3. extractionthe filtrate is extracted with ethyl acetate and sodium carbonate solution
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with ethyl acetate/petroleum ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-59dc08a3d9ec4189a9411ef1c988f31b
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080743

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