Hydrogen Bromide → HCID 58452703, compound

Participants

Reaction Conditions

Reaction Steps

48% hydrobromic acid (1.5 mL) was added to a solution of (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-[4-(dimethylamino)butyl]-6-methoxypyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one in 1,4-dioxane (2 mL), and the mixture was stirred at 65° C. for 30 minutes. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. A solution of the residue in trifluoroacetic acid (4 mL) and anisole (2 mL) was stirred at 80° C. for five hours. The reaction solution was poured into saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:1→3:1) and solidified with diethyl ether-hexane to give the title compound as a light yellow amorphous (13 mg, 12% (four steps)).

Provenance & Evidence