Ethyl Acetate → (E)-(6S*,9aR*)-6-(3-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

HRID 553908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553908
O.[OH-].[Li+].[F:4][C:5]1[CH:6]=[C:7]([C@@H:11]2[CH2:20][CH2:19][CH2:18][C@H:17]3[N:12]2[C:13](=[O:29])[CH:14](P(=O)(OCC)OCC)[CH2:15][CH2:16]3)[CH:8]=[CH:9][CH:10]=1.[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:6]=[C:7]([C@@H:11]2[CH2:20][CH2:19][CH2:18][C@H:17]3[N:12]2[C:13](=[O:29])/[C:14](=[CH:35]/[C:34]2[CH:37]=[CH:38][C:39]([N:40]4[CH:44]=[C:43]([CH3:45])[N:42]=[CH:41]4)=[C:32]([O:31][CH3:30])[CH:33]=2)/[CH2:15][CH2:16]3)[CH:8]=[CH:9][CH:10]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612701diethyl[(6S*,9aR*)-6-(3-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate

Produkt 1

HCID 24780163(E)-(6S*,9aR*)-6-(3-fluorophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-oneAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (220 mg) was added to a mixed solution of diethyl [(6S*,9aR*)-6-(3-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate (670 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (378 mg) in tetrahydrofuran (15 mL) and ethanol (5 mL) at room temperature, and the reaction solution was stirred at room temperature for one hour. 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 583 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-a4b9b2248f8d48d7af679f11af3583f2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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