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

HRID 553904Notes

Reaction equation

HRID 553904 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

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-(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.

Workup

  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)

Sources & evidence

ORD record
ord-be19b1ebbf144883b130dc509716ec8c
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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