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Water → (E)-(6S,8S,9aR)-8-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one

HRID 553947
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553947
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[CH:12]=[C:13]([C@@H:19]2[CH2:28][C@H:27](O)[CH2:26][C@@H:25]3[N:20]2[C:21](=[O:45])/[C:22](=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([N:37]4[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]4)=[C:33]([O:43][CH3:44])[CH:32]=2)/[CH2:23][CH2:24]3)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].O.C(OCC)(=O)C>ClCCl>[F:7][C@H:27]1[CH2:26][C@@H:25]2[N:20]([C:21](=[O:45])/[C:22](=[CH:30]/[C:31]3[CH:36]=[CH:35][C:34]([N:37]4[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]4)=[C:33]([O:43][CH3:44])[CH:32]=3)/[CH2:23][CH2:24]2)[C@H:19]([C:13]2[CH:14]=[C:15]([F:18])[C:16]([F:17])=[C:11]([F:10])[CH:12]=2)[CH2:28]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluorideHCID 24781747(E)-(6S*,8R*,9aR*)-6-(3,4,5-trifluorophenyl)-8-hydroxy-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

Produkt 1

HCID 24780877
(E)-(6S,8S,9aR)-8-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diethylaminosulfur trifluoride (13.2 μL) was added to a solution of (E)-(6S,8R,9aR)-6-(3,4,5-trifluorophenyl)-8-hydroxy-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one that is an optically active compound obtained above with a retention time of 4.8 minutes (10 mg) in dichloromethane (2.0 mL) under ice-cooling, and the reaction solution was stirred for two hours. Crushed ice, water, and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 5.9 mg of the title optically active compound. The property values of the optically active compound are as follows.

Aufarbeitung

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)
  7. customto obtain 5.9 mg of the title optically active compound

Quellen und Nachweise

ORD-Eintrag
ord-6ca660ae38aa4007ba21e6b5ce977209
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08048878B2

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