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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 553910Generated: October 31, 2026

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

https://huagongshe.com/reaction/553910

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-[(2R*,6S*)-2-(2-fluorophenyl)-6-vinylpiperidin-1-yl]-3-buten-1-oneHCID 69073469—
CatalystBenzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)rutheniumHCID 12045765—
SolventDichloromethaneHCID 6344—
Product(6R*,9aS*)-6-(2-fluorophenyl)-3,6,7,8,9,9a-hexahydroquinolizin-4-oneHCID 6907450592.8%

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08048878B2
Source datasetuspto-grants-2011_11
ORD IDord-91951e02c73b429d830f4b40f563703c
Source noteuspto-grants-2011_11