Methanol → HCID 86592081, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of p-toluenesulfonylmetyl isocyanide (0.94 g, 4.8 mmol) in 1,2-dimethoxyethane (20 ml) were added potassium t-butoxide (0.90 g, 8 mmol) and tert-butyl(4-butoxy-6-formyl-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (1.78 g, 4 mmol) at −70° C., and the mixture was stirred at −70° C. for 1 h. To the mixture was added methanol (30 ml), and the mixture was refluxed for 30 min. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl[4-butoxy-6-(cyanomethyl)-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.66 g, 36.3%) as an amorphous solid.

Provenance & Evidence