phenyl N-benzyloxycarbamate → 1-(N-benzyloxycarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

Participants

Reaction Steps

3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (600 mg, 2 mmole) and phenyl N-benzyloxycarbamate (490 mg, 2.01 mmole) were dissolved into 8 ml of pyridine and the solution was heated under reflux for 12 hours. The reaction mixture was evaporated and the obtained residue was dissolved into ethyl acetate, which was washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=10:1) and recrystallized from dichloromethane/n-hexane, whereby 550 mg of the objective compound (Ia-10) was obtained in 61% yield.

Provenance & Evidence