反应详情

To a stirred solution of tert-butyl 3-(hydroxy(phenyl)methyl)pyrrolidine-1-carboxylate (205 mg, 0.74 mmol) and 4-methoxybutyl iodide (750 mg, 3.5 mmol) in dry THF (5 mL) under N2 was added 60& NaH in oil (0.14 g, 3.5 mmol). H2 evolution occurred. The mixture was heated at reflux for 8 h. The mixture was cooled, diluted with ether (90 mL), and washed with water (25 mL) and brine (25 mL), and dried over MgSO4. Removal of the solvent left an oil which was purified by flash chromatography on a 12-g silica cartridge eluted with a 0 to 100% EtOAc in hexanes gradient to afford tert-butyl 3-((4-methoxybutoxy)(phenyl)methyl)pyrrolidine-1-carboxylate (47 mg, 17%) as an oil.

1. temperatureThe mixture was heated
2. temperatureat reflux for 8 h
3. temperatureThe mixture was cooled
4. washwashed with water (25 mL) and brine (25 mL)
5. dry with materialdried over MgSO4
6. customRemoval of the solvent
7. waitleft an oil which
8. customwas purified by flash chromatography on a 12-g silica cartridge
9. washeluted with a 0 to 100% EtOAc in hexanes gradient