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 553878Notes

Reaction equation

HRID 553878 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

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-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.

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-0228d10282f04927864f637604ba8f56
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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