1,1'-Carbonyldiimidazole → (E)-(6S*,9aR*)-6-(4-cyanophenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one

Participants

Reaction Steps

Dess-Martin periodinane (37 mg) was added to a solution of (E)-(6S*,9aR*)-6-(4-hydroxymethylphenyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one (20 mg) in methylene chloride (2 mL), and the reaction solution was stirred at room temperature for 30 minutes. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain a crude aldehyde compound. Hydroxylamine hydrochloride (9 mg) and sodium acetate (11 mg) were added to a solution of the resulting crude aldehyde compound in ethanol (3 mL), and the reaction solution was stirred at room temperature for 12 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain a crude oxime compound. To a solution of the resulting crude oxime compound in THF (5 mL), 1,1′-carbonyldiimidazole (70 mg) was added, and the reaction solution was heated to reflux for five hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=1:1->ethyl acetate) to obtain 6 mg of the title compound. The property values of the compound are as follows.

Provenance & Evidence