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

HRID 553894Notes

Reaction equation

HRID 553894 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([CH:17]=[CH2:18])[N:12]2[C:19](=[O:23])[CH2:20]C=C)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]>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>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]3[N:12]2[C:19](=[O:23])[CH2:20][CH:18]=[CH:17]3)=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 690737051-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Product 1

HCID 69074738(6R*,9aS*)-6-(4-carbomethoxyphenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneYield 56.7%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 1-[(2R*,6S*)-2-(4-carbomethoxyphenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one (281 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (53 mg) in methylene chloride (150 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 145 mg of the title compound. The property value of the compound is as follows.

Workup

  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)

Sources & evidence

ORD record
ord-64d594c76af84b72b2893ea77f0be7c0
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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