Triethylamine → (6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-one

HRID 553910Notes

Reaction equation

HRID 553910 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10](C=C)[N:9]1[C:16](=[O:20])[CH2:17][CH:18]=[CH2:19].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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]2[N:9]1[C:16](=[O:20])[CH2:17][CH:18]=[CH:19]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 690734691-[(2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one

Product 1

HCID 69074505(6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneYield 92.8%

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-(2-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-one (442 mg) and tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium (IV) dichloride (69 mg) in methylene chloride (180 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 368 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-91951e02c73b429d830f4b40f563703c
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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