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

Participants

Reaction Steps

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.

Provenance & Evidence