Methanol → 2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (2.54 g), palladium(II) acetate (52 mg), 1,1′-bis(diphenylphosphino)ferrocene (125 mg), triethylamine (1.6 ml), DMF (13 ml) and methanol (13 ml) was stirred at 60° C. for 72 hrs. under 1 atm carbon monoxide. The reaction mixture was concentrated and water was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=2:1) and recrystallized (ethyl acetate-hexane) to give the title compound (1.82 g).

Provenance & Evidence