反应详情

An oven dried 250.0 mL three necked round bottom flask equipped with a mechanical stirrer, thermometer, addition funnel with a continuous nitrogen blanket is charged with (2R)-2-phenylpropan-1-ol (2.0 mL, 14.32 mmol), phthalimide (2.1 g, 14.32 mmol), triphenylphosphine (5.63 g, 21.48 mmol) and THF (70.0 mL). To this solution at room temperature was then added a solution of diethylazodicarboxylate (3.38 mL, 21.48 mmol) dissolved in THF (10.0 mL) over a period of 15-20 minutes (reaction exothermed slightly to 50° C. by the end of addition went from clear to reddish color). Stirred reaction to room temperature overnight). To the red solution was added water (50.0 mL) and the organic extracted with chloroform (140.0 mL). Dried the organic solution with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to an oil. To the oil was added heptane (150.0 mL) with stirring. Filtered of precipitates, then concentrated filtrate to an oil. Plug filtration of the oil over silica gel with 1:1 ethylacetate/hexane and concentrating product fractions afforded the intermediate title compound, 2((2R)-2-phenylpropyl)isoindoline-1,3-dione, (4.27 g, 96%) as an oil which solidified on equilibrating to room temperature; 1H nmr (CDCl3, 300 MHz) δ 1.3 (d, 3H), 3.3-4.0 (m, 1H), 3.7-3.9 (m, 2H), 7.1-7.3 (aromat. m, 2H), 7.63-7.7 (aromat. m, 2H), 7.8-7.85 (aromat. m, 4H).

1. dry with materialAn oven dried 250.0 mL three necked round bottom flask
2. customequipped with a mechanical stirrer
3. additionthermometer, addition funnel with a continuous nitrogen blanket
4. customreaction exothermed slightly to 50° C.
5. additionby the end of addition
6. customreaction to room temperature overnight)
7. extractionthe organic extracted with chloroform (140.0 mL)
8. dry with materialDried the organic solution with anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure to an oil
11. additionTo the oil was added heptane (150.0 mL)
12. stirringwith stirring
13. filtrationFiltered
14. customof precipitates
15. filtrationPlug filtration of the oil over silica gel with 1:1 ethylacetate/hexane
16. concentrationconcentrating product fractions