1-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one → (4R*,10aS*)-4-(4-fluorophenyl)-1,3,4,7,8,10a-hexahydro-2H-pyrido[1,2-a]azepin-6-one

HRID 553884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553884
[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:21])[CH2:17][CH2:18][CH:19]=[CH2:20])=[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[N:9]3[C:16](=[O:21])[CH2:17][CH2:18][CH:19]=[CH:20][C@@H:10]3[CH2:11][CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 690774171-[(2R*,6S*)-2-(4-fluorophenyl)-6-vinylpiperidin-1-yl]-4-penten-1-one

Produkt 1

HCID 69071429(4R*,10aS*)-4-(4-fluorophenyl)-1,3,4,7,8,10a-hexahydro-2H-pyrido[1,2-a]azepin-6-oneAusbeute 52,7 %

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]-4-penten-1-one (307 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (64 mg) in methylene chloride (150 mL) was heated under reflux for 25 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 146 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperatureunder reflux for 25 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-86cd2c099f0847789b3fe901c6072609
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048878B2

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