(2-Bromoethyl)cyclohexane → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25787

Reaktionsgleichung

Reaktionsgleichung von HRID 25787
C(OC(N1C2C(=CC(C3C=CC=CC=3OC)=CC=2)C(C(O)C)=CC1(C)C)=O)(C)(C)C.[CH:31]1([CH2:37][CH2:38][O:39][CH:40]([C:42]2[C:51]3[C:46](=[CH:47][CH:48]=[C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=4[O:58][CH3:59])[CH:50]=3)[NH:45][C:44]([CH3:61])([CH3:60])[CH:43]=2)[CH3:41])CCCC[CH2:32]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1(CCBr)CCCCC1>C1COCC1>[CH2:38]([O:39][CH:40]([C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[O:58][CH3:59])[CH:50]=2)[NH:45][C:44]([CH3:61])([CH3:60])[CH:43]=1)[CH3:41])/[CH:37]=[CH:31]/[CH3:32]

Komponenten

5

Edukt 3

HCID 15440(2-Bromoethyl)cyclohexaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 691539464-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 49 mg of 2-cyclohexylethyl bromide to give the alkylated product, which was deprotected to yield 31 mg of title compound as an oil.

Aufarbeitung

  1. customto give the alkylated product, which

Quellen und Nachweise

ORD-Eintrag
ord-ce9a7ee077a34850b30661c174215de3
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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