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 553884ノート

反応式

HRID 553884 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: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

参加物

4

反応物 1

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

生成物 1

HCID 69071429(4R*,10aS*)-4-(4-fluorophenyl)-1,3,4,7,8,10a-hexahydro-2H-pyrido[1,2-a]azepin-6-one収率 52.7%

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]-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.

後処理

  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)

出典と根拠

ORDレコード
ord-86cd2c099f0847789b3fe901c6072609
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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