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

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Reaction Steps

To a solution of 2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid dimethyl ester (1.63 g) in THF (16 ml) were added methanol (16 ml) and 8N-aqueous sodium hydroxide solution (0.8 ml) at room temperature, and the mixture was stirred for 18 hrs. The reaction mixture was concentrated under reduced pressure and water and 1N-hydrochloric acid (7 ml) were added to the residue. The aqueous layer was acidified and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methylene chloride was added to the residue and insoluble material was removed from the mixture. The filtrate was concentrated and recrystallized (ethyl acetate-hexane) to give the title compound (1.16 g).

Provenance & Evidence