Boron tribromide → HCID 19029813, compound

Participants

Reaction Conditions

Reaction Steps

In 4 ml of dichloromethane was dissolved 150 mg of the compound obtained in Example 8, and under ice-cooling, 1.2 ml of a solution (1.0M) of boron tribromide in n-hexane was added. The mixture was stirred at 0° C. for 1.5 hours, and then it was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. In 10 ml of ethanol was dissolved 34 mg of the resulting crude crystals, and after addition of an aqueous solution (6.8 ml) containing 83 mg of potassium dinitrosulfonate and 34 mg of dipotassium hydrogen phosphate, the mixture was stirred at room temperature for 13 hours. The reaction mixture was then diluted with water and extracted with chloroform. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent=ethyl acetate:n-hexane=1:9) to provide 1 mg of the object compound.

Provenance & Evidence