A kind of preparation method of chiral o-diamine compound
A technology for ortho-diamine compounds, applied in the field of preparation of chiral ortho-diamine compounds, to achieve the effects of mild reaction conditions, rich product structure types, and simple reaction raw materials
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Embodiment 1
[0029] Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL) were successively added to a dry Schlenk tube, and after stirring at room temperature for 30 minutes 2-Phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and aniline (0.1mmol dissolved in 0.25mL dry m-xylene) were added in sequence, and the reaction was stirred at 15°C for 10 hours (monitored by TLC). After the reaction was completed, saturated aqueous sodium bicarbonate solution (5 mL) was added to terminate the reaction, extracted with ethyl acetate (5 mL×3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing agent, and the product is separated by 300-400 mesh silica gel column chromatography, and its enantiomeric ratio (e.r. value) is determined by the HPLC method of a chiral stationary phase, and th...
Embodiment 2
[0033]Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry m-xylene (0.25 mL) were successively added to a dry Schlenk tube, and after stirring at room temperature for 30 minutes Add 2-phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and 4-methoxyaniline (0.1mmol dissolved in 0.25mL dry m-xylene) in sequence, and then stir the reaction at 15°C for 10 hours (TLC monitoring). After the reaction was completed, saturated aqueous sodium bicarbonate solution (5 mL) was added to terminate the reaction, extracted with ethyl acetate (5 mL×3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing solvent, and the product is separated by 300-400 mesh silica gel column chromatography, and the enantiomeric ratio (e.r. value) is determined by the HPLC method of a chiral stationary phase, and th...
Embodiment 3
[0037] The operation of reaction is with embodiment 2, but solvent used is different, and concrete operation is as follows:
[0038] Under an argon atmosphere, silver hexafluoroantimonate (0.0025 mmol), (S)-DTBM-SEGPHOS (0.00375 mmol) and dry dichloromethane (0.25 mL) were successively added to a dry Schlenk tube, and stirred at room temperature for 30 minutes Add 2-phenyl-N-p-toluenesulfonyl aziridine (0.22mmol) and 4-methoxyaniline (0.1mmol dissolved in 0.25mL dry dichloromethane) in sequence, and then stir the reaction at 15°C for 12 hours (TLC monitoring). After the reaction was completed, saturated aqueous sodium bicarbonate solution (5 mL) was added to terminate the reaction, extracted with ethyl acetate (5 mL×3), dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. The mixed solvent of 1 (containing 0.5v% triethylamine) is used as a developing solvent, and the product is separated by 300-400 mesh silica g...
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