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 553855ノート

反応式

HRID 553855 の反応式
[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

参加物

4

反応物 1

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

生成物 1

HCID 69073672(6R*,9aS*)-6-(4-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one収率 82.4%

試薬・触媒・溶媒 2

HCID 12045765Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)ruthenium触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cdde13fb12ca42eeb4f8d1f0d86359a2
出典データセット
uspto-grants-2011_11
特許番号
US08048878B2

反応ノート

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