Water → Methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]pentanoate (840 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (874 mg), and the mixture was heated at 65° C. for 3 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the residue, and then the obtained residue was washed with hexane-ethyl acetate to give methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (741 mg) as yellow crystals.

Provenance & Evidence