1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one → (6R*,9aS*)-6-(4-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one

HRID 553855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553855
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10](C=C)[N:9]2[C:16](=[O:20])[CH2:17][CH:18]=[CH2:19])=[CH:4][CH:3]=1>C(Cl)Cl.CC1C=C(C)C(N2[CH-]N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]3[N:9]2[C:16](=[O:20])[CH2:17][CH:18]=[CH:19]3)=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 690774971-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Produkt 1

HCID 69073672(6R*,9aS*)-6-(4-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12045765Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)rutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one (744 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (116 mg) in methylene chloride (250 mL) was heated under reflux for two hours. The reaction solution was left to cool to room temperature and then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate) to obtain 550 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. waitThe reaction solution was left
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=4:1->ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cdde13fb12ca42eeb4f8d1f0d86359a2
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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