Dimethylformamide → 6-bromo-3-hydroxymethyl-2-(4-methanesulfonylbenzyl)-4-phenyl-2H-isoquinolin-1-one

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Reaction Steps

DMF (0.1 ml) was added to a suspension of 6-bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (5.5 g) in THF (55 ml), and oxalyl chloride (1.9 ml) was added dropwise under ice-cooling. The reaction mixture was allowed to warm to room temperature, stirred for 30 min., and concentrated under reduced pressure. The residue was suspended in a mixture of THF (90 ml) and 1,2-dimethoxyethane (90 ml), and under ice-cooling sodium borohydride (1.62 g) and methanol (3 ml) were added. The mixture was allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was poured into water under ice-cooling. 10% Hydrochloric acid was added to acidify the aqueous layer, and THF and methanol were evaporated under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diisopropyl ether to give the title compound (5.3 g).

Provenance & Evidence