Triethylamine → (6R*,9aS*)-6-(3-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one

HRID 553904ノート

反応式

HRID 553904 の反応式
[F:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(N(CC)CC)C>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]=[C:4]([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:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 8471TriethylamineHCID 690769341-[(2R*,6S*)-2-(3-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

生成物 1

HCID 69073906(6R*,9aS*)-6-(3-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one収率 87.3%

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-(3-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one (587 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (92 mg) in methylene chloride (250 mL) was heated under reflux in a nitrogen atmosphere for two hours. The reaction solution was left to cool to room temperature. Then, triethylamine (0.5 mL) was added thereto, and the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 460 mg of the title compound. The property values of the compound are as follows.

後処理

  1. temperatureunder reflux in a nitrogen atmosphere for two hours
  2. waitThe reaction solution was left
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

出典と根拠

ORDレコード
ord-be19b1ebbf144883b130dc509716ec8c
出典データセット
uspto-grants-2011_11
特許番号
US08048878B2

反応ノート

読み込み中…