反应详情

To a suspension of 2-((1R,2S,4R,5S)-5-(tert- butyldiphenylsilyloxy)bicyclo[2.2.1]-heptan-2-yl)isoindoline-1,3-dione (4.60 g, 9.28 mmol) in ethanol (anhydrous, 100 mL) was added anhydrous hydrazine (0.44 mL, 13.9 mmol). After refluxing under nitrogen for 3 h, the mixture was cooled to ambient temp. The white solid was removed by filtration, and the filtrate was concentrated in vacuo to give an off-white solid, which was stirred with benzoyl isothiocyanate (1.62 mL, 12.1 mmol) in chloroform (100 mL) at ambient temp. overnight. The reaction mixture was diluted with dichloromethane (50 mL) and the solid was removed by filtration. The filtrate was concentrated to give an off-white solid, which was stirred with potassium carbonate (3.85 g, 27.8 mmol) in methanol (100 mL) at ambient temp. for 30 min. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and water. The organic portion was separated, washed with brine, and conc. in vacuo. The residue was purified by flash column chromatography (0 to 60% of EtOAc in hexanes) to give the title compound as a white solid. MS m/z: 425.2 (M+H)+.

1. temperatureAfter refluxing under nitrogen for 3 h
2. customThe white solid was removed by filtration
3. concentrationthe filtrate was concentrated in vacuo
4. customto give an off-white solid, which
5. customthe solid was removed by filtration
6. concentrationThe filtrate was concentrated
7. customto give an off-white solid, which
8. customThe solvents were removed in vacuo
9. customthe residue was partitioned between EtOAc and water
10. customThe organic portion was separated
11. washwashed with brine
12. customThe residue was purified by flash column chromatography (0 to 60% of EtOAc in hexanes)