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

Participants

Reaction Steps

Lithium hydroxide monohydrate (220 mg) was added to a mixed solution of diethyl [(6S*,9aR*)-6-(3-fluorophenyl)-4-oxooctahydroquinolizin-3-yl]phosphonate (670 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (378 mg) in tetrahydrofuran (15 mL) and ethanol (5 mL) at room temperature, and the reaction solution was stirred at room temperature for one hour. Ethyl acetate was added to the reaction solution, which was then sequentially washed with saturated sodium bicarbonate water and brine. 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 system) to obtain 583 mg of the title compound. The property values of the compound are as follows.

Provenance & Evidence