Hydrazine hydrate (1:1) → HCID 22176261, compound

Participants

Reaction Steps

A mixture of tert-butyl{6-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl}methylcarbamate (0.85 g, 1.5 mmol), and hydrazine monohydrate (0.6 mL, 12 mmol) in ethanol (20 mL) and tetrahydrofuran (10 mL) was stirred at room temperature for 17 h. The reaction mixture was filtered, and the filtrate was concentrated. After the residue was dissolved in ethyl acetate (50 mL), the solution was filtrated to remove insoluble material. The filtrate was concentrated to give tert-butyl[6-(aminomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.82 g) as a crude pale yellow oil. To a solution of the crude oil (0.16 g) in tetrahydrofuran (2 mL) was added acetic anhydride (0.034 mL, 0.36 mmol), and then the mixture was stirred at room temperature for 4 h. The reaction mixture was washed with water (4 mL) and concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v)) to give tert-butyl{6-[(acetylamino)methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.090 g, 63%) as a pale yellow solid.

Provenance & Evidence