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

HRID 553878
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HRID 553878 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][C@@H:11](C=C)[N:10]2[C:17](=[O:21])[CH2:18][CH:19]=[CH2:20])=[CH:5][CH:4]=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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]3[N:10]2[C:17](=[O:21])[CH2:18][CH:19]=[CH:20]3)=[CH:7][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 690748621-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

생성물 1

HCID 69072392(6R*,9aS*)-6-(4-methoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one수율 31.1%

시약·촉매·용매 2

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

실험 절차

A solution of 1-[(2R*,6S*)-2-(4-methoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one (100 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (30 mg) in methylene chloride (50 mL) was heated under reflux for 1.5 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 28 mg of the title compound. The property values of the compound are as follows.

후처리

  1. temperatureunder reflux for 1.5 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)

출처 및 근거

ORD 기록
ord-0228d10282f04927864f637604ba8f56
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048878B2

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