反应详情

To a solution of 3-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide (2.57 g, 8.08 mmol) in THF (30 mL) was added a solution of borane in THF (24.3 ml, 24.3 mmol, 1M) and the resulting mixture was stirred at rt for 2 hrs. The mixture was then refluxed for 2 hrs. A solution of borane in THF (10.0 ml, 10.0 mmol, 1M) was added again and the mixture was refluxed for an additional 5 hrs. The reaction was quenched with HCl 5 N. Then the solution was made basic by the addition of an aqueous solution of NaOH (5N) and extracted with Et2O (3×). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (20/80)) gave 2.1 g (86%) of the title compound as a white solid.

1. temperatureThe mixture was then refluxed for 2 hrs
2. temperaturethe mixture was refluxed for an additional 5 hrs
3. customThe reaction was quenched with HCl 5 N
4. additionThen the solution was made basic by the addition of an aqueous solution of NaOH (5N)
5. extractionextracted with Et2O (3×)
6. dry with materialThe combined organic layers were dried over MgSO4
7. customthe solvents were removed under reduced pressure
8. customPurification by flash chromatography on silicagel (EtOAc/c-Hex (20/80))