反应详情

Boron tribromide (6.92 mmol) was added dropwise into a solution of (S)—N-(2-[4-methoxy-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide (1.00 g. 3.46 mmol) in methylene chloride (15 mL) at about −50° C. The mixture was stirred for 2 hours at temperatures ranging from −50 to 0° C. Crushed ice was added and the mixture was stirred for further 2 hours at room temperature, followed by extracting with methanol-chloroform. The extracted solution was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 320 mg, 34%) as a white powder. This compound is also referred to as metabolite 1.

1. customranging from −50 to 0° C
2. additionCrushed ice was added
3. stirringthe mixture was stirred for further 2 hours at room temperature
4. extractionby extracting with methanol-chloroform
5. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
6. distillationby distilling off the solvent under reduced pressure
7. customThe residue was purified by means of silica gel column chromatography (ethyl acetate)