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Ethyl Acetate → 6-(2-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

HRID 553914
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553914
O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C@@H:11]1[CH2:20][CH2:19][CH2:18][C@H:17]2[N:12]1[C:13](=[O:29])[CH:14](P(=O)(OCC)OCC)[CH2:15][CH2:16]2.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[N:40]1[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]1)[CH:35]=O.C(OCC)(=O)C>O1CCCC1.C(O)C>[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]1[CH2:20][CH2:19][CH2:18][CH:17]2[N:12]1[C:13](=[O:29])[C:14](=[CH:35][C:34]1[CH:37]=[CH:38][C:39]([N:40]3[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]3)=[C:32]([O:31][CH3:30])[CH:33]=1)[CH2:15][CH2:16]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612702diethyl[(6S*,9aR*)-6-(2-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

Produkt 1

HCID 866325466-(2-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one
Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (169 mg) was added to a mixed solution of diethyl [(6S*,9aR*)-6-(2-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate (501 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (290 mg) in tetrahydrofuran (12 mL) and ethanol (4 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate was added to the reaction solution, which was then sequentially washed with saturated sodium bicarbonate water and brine. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 483 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. washwas then sequentially washed with saturated sodium bicarbonate water and brine
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-4c7a53c4b7ed4088b8627a656bad94d6
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048878B2

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