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Preparation method of R-5, 6-dimethoxy-1-aminoindane
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A technology of dimethoxyl and aminoindane, which is applied in the field of preparation of optically pure chiral compounds, achieving the effects of mild process conditions, easy separation and recycling, and stable chemical properties
Inactive Publication Date: 2015-12-16
吴玲
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Problems solved by technology
In the existing research on 5,6-dimethoxy-1-aminoindan, there are few reports on how to prepare optically pure R-5,6-dimethoxy-1-aminoindan
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Embodiment 1
[0008] (1) Preparation of 5,6-dimethoxy-1-indanone oxime
[0009] In a 1000ml round-bottomed flask, add 600ml methanol, 192g (1.0mol) 5,6-dimethoxy-1-indanone, 70g (1.0mol) hydroxylaminehydrochloride, 98.4g (1.2mol) sodium acetate, reflux to react to Disappearance of 5,6-dimethoxy-1-indanone was detected by spot plate. After cooling, 5000 ml of water was added to the system under stirring, and a large amount of white solid was precipitated, which was filtered and dried to obtain 194.2 g of 5,6-dimethoxy-1-indanone oxime with a yield of 93.8%.
[0010] (2) Preparation of 5,6-dimethoxy-1-aminoindan
[0011] In a 2000ml autoclave, add 1300ml methanol, 194.2g 5,6-dimethoxy-1-indanone oxime, 20g Raney nickel, seal the autoclave and replace the air, then feed 10g ammonia, and finally hydrogen and keep it. Pressure 2.5MPa, react at 60℃ for 6h, 5,6-dimethoxy-1-indanone oxime was converted into 5,6-dimethoxy-1-aminoindane, filtered and concentrated to obtain 5,6- Dimethoxy-1-aminoi...
Embodiment 2
[0019] (1) Preparation of 5,6-dimethoxy-1-indanone oxime
[0020] In a 2000ml round-bottomed flask, add 700ml methanol, 192g (1.0mol) 5,6-dimethoxy-1-indanone, 183.8g (1.2mol) hydroxylamine hydrochloride, 123g (1.5mol) sodium acetate, reflux to react to Disappearance of 5,6-dimethoxy-1-indanone was detected by spot plate. Under stirring, 5000 ml of water was added to the system, and a large amount of white solid was precipitated, which was filtered and dried to obtain 194.6 g of 5,6-dimethoxy-1-indanone oxime with a yield of 94.0%.
[0021] (4) Preparation of 5,6-dimethoxy-1-aminoindan
[0022] In a 2000ml autoclave, add 1200ml methanol, 194.6g 5,6-dimethoxy-1-indanone oxime, 30g Raney nickel, seal the autoclave and replace the air, then introduce 15g of ammonia gas, and finally hydrogen and keep it. Pressure 2.0MPa, react at 70℃ for 3h, 5,6-dimethoxy-1-indanone oxime was converted into 5,6-dimethoxy-1-aminoindane, filtered and concentrated to obtain 5,6- Dimethoxy-1-aminoi...
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Abstract
The invention discloses a method for preparing R-5, 6-dimethoxy-1-aminoindane via 5, 6-dimethoxy-1-indanone. The method includes the operations: reacting the 5, 6-dimethoxy-1-indanone with hydroxylamine and alkali to generate a ketoxime, and subjecting the ketoxime to hydrogenation reduction under the action of a hydrogenation catalyst to generate 5, 6-dimethoxy-1-aminoindane; reacting the 5, 6-dimethoxy-1-aminoindane with a chiral resolving agent in an alcoholsolvent to obtain a resolving agent enantiomer salt of R-5, 6-dimethoxy-1-aminoindane, dissolving the salt in water after recrystallization, alkalifying the salt to obtain the R-5, 6-dimethoxy-1-aminoindane having an ee value up to above 99%; combining and acidifying solutions containing the resolving agent to recycle the resolving agent. The method provided by the invention allows operational simplicity and high resolving efficiency, the resolving agent and resolving solvents are easy to recycle and use indiscriminately, and the method has low environmental pollution and is suitable for industrial production.
Description
technical field [0001] The invention relates to a preparation method of an optically pure chiral compound, in particular to a preparation method of R-5,6-dimethoxy-1-indanone using 5,6-dimethoxy-1-indanone as a starting material Methods for aminoindanes. Background technique [0002] R-5,6-dimethoxy-1-aminoindan is a very important class of chiral pharmaceutical intermediates. In the existing researches on 5,6-dimethoxy-1-aminoindane, there are few reports on how to prepare optically pure R-5,6-dimethoxy-1-aminoindane. How to obtain an efficient and convenient method for preparing R-5,6-dimethoxy-1-aminoindane is the problem to be solved by the present invention. SUMMARY OF THE INVENTION [0003] The object of the present invention is to provide a method for preparing R-5,6-dimethoxy-1-aminoindan from 5,6-dimethoxy-1-indanone, the specific operation is 5,6-dimethoxy-1-aminoindan Methoxy-1-indanone reacts with hydroxylamine and base in alcoholsolvent to form ketoxime, a...
Claims
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