Methyl iodide → (E)-(6S,8R,9aR)-8-methoxy-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one

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Reaction Steps

Sodium hydride (4.0 mg) and iodomethane (6.3 μL) were added to a solution of (E)-(6S,8R,9aR)-6-(3,4,5-trifluorophenyl)-8-hydroxy-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]octahydroquinolizin-4-one that is an optically active compound obtained in Example 71 with a retention time of 4.8 minutes (10 mg) in THF (2.0 mL) under ice-cooling, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous 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->ethyl acetate-methanol system) to obtain 3.05 mg of the title optically active compound. The property values of the optically active compound are as follows.

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