反应详情

温度

80 °C

A mixture of 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl trifluoromethanesulfonate (5.18 g, 16.59 mmol), diphenylmethanimine (3.61 g, 19.91 mmol), Pd2(dba)3 (0.759 g, 0.83 mmol), BINAP (1.033 g, 1.66 mmol), sodium tert-butoxide (2.391 g, 24.88 mmol) and toluene (75 mL) was stirred at 80° C. for 2 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in THF (200 mL), LN hydrochloric acid (83 mL, 82.94 mmol) was added thereto, and the mixture was stirred at room temperature for 30 min, and basified with 1N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane) to give 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine (1.92 g, 10.71 mmol, 65%) as an orange oil.

1. extractionthe mixture was extracted with ethyl acetate
2. dry with materialThe organic layer was dried over magnesium sulfate
3. customthe solvent was evaporated under reduced pressure
4. dissolutionThe obtained residue was dissolved in THF (200 mL)
5. stirringthe mixture was stirred at room temperature for 30 min
6. extractionThe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried over magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane)