Ethyl Acetate → Gamma-secretase modulators

Participants

Reaction Steps

Lithium hydroxide monohydrate (63.4 mg) was added to a mixed solution of diethyl [(4R,9aS)-6-oxo-4-(3,4,5-trifluorophenyl)octahydropyrido[2,1-c][1,4]oxazin-7-yl]phosphonate (372 mg) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (229 mg) in tetrahydrofuran (6 mL) and ethanol (2 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with 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 163.2 mg of the title compound.

Provenance & Evidence