A kind of preparation method of chiral amine compound
A compound and chiral secondary amine technology, applied in the field of preparation of chiral amine compounds, can solve the problems of human health hazards, heavy metal residues, unsatisfactory product diastereoselectivity, etc., and achieve high diastereoselectivity , mild conditions, high reaction atom economy effect
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Embodiment 1
[0036] Embodiment 1: double-( S The preparation of )-(1-phenylethyl)amine (Ia)
[0037] The preparation steps are:
[0038] (1) 1.2g acetophenone (10 mmol), 1.4g ( S )- α - Phenylethylamine (12 mmol), 0.024 g of triphenylborane (0.1 mmol) and 4.8 g of anhydrous magnesium sulfate were added to 50 mL of chloroform solvent, and the reaction was stirred at 30 ° C for 6 hours;
[0039] (2) Add 1.8 g of triethylsilane (15 mmol) to the reaction system in step (1), continue stirring at 30°C for 3 hours, filter, and wash the filter cake with 15 mL of ethyl acetate for 3 times; The filter cake washing liquid was evaporated and concentrated to obtain the crude product ( de =91%), and then use the mixed solvent of petroleum ether and ethyl acetate as the eluent with a volume ratio of 5:1, and quickly separate through silica gel column chromatography to obtain the desired bis-( S )-(1-phenylethyl)amine (Ia) product to obtain 2.2 g of colorless liquid, yield 94%. pair-( S The struct...
Embodiment 2
[0043] Embodiment 2: ( S )-1-phenyl- N -(( S )-1-(4-methoxyphenyl) ethyl) ethylamine (Ib) preparation
[0044] The preparation steps are:
[0045] (1) Mix 1.3g p-methylacetophenone (10 mmol), 1.3g ( S )- α - Phenylethylamine (11 mmol), 0.025 g of tris(pentafluorophenyl) borane (0.05 mmol) and 2.6 g of anhydrous sodium sulfate were added to 50 mL of tetrahydrofuran solvent, and the reaction was stirred at 100 ° C for 2 hours;
[0046] (2) Add 2.0 g of trichlorosilane (20 mmol) to the reaction system in step (1), and continue to stir and react at 10°C for 5 hours. After the reaction was finished, filter, and the filter cake was washed 3 times with 15 mL of ethyl acetate; the resulting filtrate and filter cake washing liquid were evaporated and concentrated to obtain the crude product ( de =91%), and then use the mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 5:1 as the eluent, and quickly separate through silica gel column chromatography to obta...
Embodiment 3
[0050] Embodiment 3: ( S )-1-phenyl- N -(( S )-1-(2-fluorophenyl) ethyl) ethylamine (Ic) preparation
[0051] The preparation steps are:
[0052] (1) Mix 1.2g o-fluoroacetophenone (10 mmol), 2.4g ( S )- α - Phenylethylamine (20 mmol), 0.024g triphenylborane (0.1 mmol) and 7.2g 4Å molecular sieves were added to 50mL n-hexane solvent, and the reaction was stirred at 60°C for 4 hours;
[0053] (2) Add 0.62 g of ammonia borane (20 mmol) to the reaction system in step (1), and continue stirring at 30°C for 6 hours. After the reaction was finished, filter, and the filter cake was washed 3 times with 15 mL of ethyl acetate; the resulting filtrate and filter cake washing liquid were evaporated and concentrated to obtain the crude product ( de =92%), and then use the mixed solvent of petroleum ether and ethyl acetate as the eluent with a volume ratio of 5:1, and quickly separate through silica gel column chromatography to obtain the desired ( S )-1-phenyl-N-(( S )-1-(2-fluorop...
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