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Water → 1-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

HRID 555325
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 555325
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[O:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[O:28])([CH3:25])([CH3:24])[CH3:23].O>C1(C)C=CC=CC=1.O1CCCC1>[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][C:12]1=[O:11])=[O:28])([CH3:25])([CH3:24])[CH3:23]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 64796HydrocarbostyrilHCID 3251421Potassium bis(trimethylsilyl)amideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

Produkt 1

HCID 669882961-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.5M Potassium bis-(trimethylsilyl)-amide in toluene (10 ml) was added dropwise at −30° C. in an argon atmosphere to a stirred solution of 2-oxo-1,2,3,4-tetrahydroquinoline (735 mg) in tetrahydrofuran (50 ml). After further cooling to −50° C. a solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (1.5 g) in tetrahydrofuran (10 ml) was added slowly. Subsequently the temperature was allowed to raise to room temperature followed by heating at 50-60° C. for 48 hours. Ice and water were added and the mixture was extracted twice with ethyl acetate. The organic phases were washed with saturated sodium chloride, dried and evaporated to leave a yellow oil which after purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent gave the desired compound as a colourless oil.

Aufarbeitung

  1. additionwas added slowly
  2. temperatureby heating at 50-60° C. for 48 hours
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic phases were washed with saturated sodium chloride
  5. customdried
  6. customevaporated
  7. customto leave a yellow oil which
  8. customafter purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-755de4918fee4d9aa5ce21b2aa2929dd
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08053446B2

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