HCID 22175437, compound → HCID 22176015, compound

Participants

Reaction Steps

Tert-butyl(2-isobutyl-6-{[methoxy(methyl)amino]carbonyl}-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.175 g, 0.355 mmol) was dissolved in tetrahydrofuran (5 mL) and a solution (0.15 mL, 0.43 mmol) of 3 M methyl magnesium bromide in diethyl ether was added dropwise under ice-cooling. This mixture was stirred at room temperature for 1 h and quenched with saturated aqueous ammonium chloride solution (5 mL). The whole was extracted with ethyl acetate (10 mL), and the organic layer was washed once each with 0.1 M aqueous citric acid solution (10 mL), saturated aqueous sodium hydrogencarbonate (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v)) to give tert-butyl(6-acetyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.132 g, 83%) as a colorless powder.

Provenance & Evidence