Ethyl Acetate → 3-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indol

HRID 2256393

Reaktionsgleichung

Reaktionsgleichung von HRID 2256393
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21][CH:22]([CH2:24][CH2:25][CH:26](Br)[CH3:27])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:26]([CH3:27])[CH2:25][CH2:24][CH:22]([Br:21])[CH3:23])[CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 912322,5-DibromohexaneHCID 10401227tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate

Produkt 1

HCID 190299193-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indolAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole (1.34 g, 4.86 mmol) in acetonitrile (50 mL) were added 2,5-dibromohexane (2.4 g, 9.72 mmol) and potassium carbonate (1.3 g, 9.72 mmol) and the resulting mixture was stirred at reflux for 60 hours. After cooling to room temperature, the solution was poured into ethyl acetate (40 mL), washed with water (40 mL), dried over sodium sulfate and evaporated to dryness. Column chromatography on silica gel using hexane/ethyl acetate (4:1, 2:1 and 1:1) provided the title compound as a syrup (0.65 g, 30%).

Aufarbeitung

  1. temperatureat reflux for 60 hours
  2. washwashed with water (40 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-221c90edee9d436da453310cff08c10e
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05654431

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