反应详情

To a suspension of (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347) (10.6 g, 23.3 mmol, 1.0 eq) in 1,4-dioxane (200 mL) and water (100 mL), OsO4 (50 mg) was added and the resulting mixture was stirred at RT for 30 min. To this mixture, NaIO4 (15 g, 69.9 mmol, 3.0 eq) was added, and then the mixture was stirred at RT for 16 h. The mixture reaction was poured into water (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-formylisoquinolin-3-yl)ethylcarbamate (348).

1. additionwas added
2. stirringthe mixture was stirred at RT for 16 h
3. customThe mixture reaction
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe organic layer was washed with water (2×100 mL) and brine (100 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo
9. customThe residue was purified by flash column chromatography on silica gel (5-20% ethyl acetate-petro ether)