Methanol → Methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl [2-isobutyl-4-(4-methylphenyl)-6-trifluoromethanesulfonyloxy-quinolin-3-yl]methylcarbamate (12.16 g, 22 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.61 g, 1.1 mmol), palladium acetate (0.25 g, 1.1 mmol), triethylamine (3.4 ml, 24.2 mmol), methanol (30 ml) and tetrahydrofuran (50 ml) was stirred in a sealed tube under a 0.5 MPa carbon monoxide atmosphere at 100° C. for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylate (6.84 g, yield 67%) as colorless crystals.

Provenance & Evidence