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The synthetic method of chiral p-methoxybenzylamine

The technology of a kind of methoxybenzylamine and the synthesis method is applied in the field of synthesis of chiral p-methoxybenzylamine, and achieves the effects of being beneficial to industrial production, easy to crystallize and purify, and easy to operate

Inactive Publication Date: 2012-02-08
BAILING PHARMA SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method will produce isomers during the condensation reduction process with chiral phenylethylamine (Tetrahedron (1985, 6005))

Method used

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  • The synthetic method of chiral p-methoxybenzylamine
  • The synthetic method of chiral p-methoxybenzylamine
  • The synthetic method of chiral p-methoxybenzylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a 10-liter four-neck flask, add 5 liters of anhydrous methanol and 1.21 kg of S-phenylethylamine, and after stirring at room temperature for 15 minutes, add 1.1 kg of acetic anhydride dropwise. After the addition is completed, stir at room temperature, concentrate after the TLC detection reaction, and obtain The solid was washed with water, and vacuum-dried to obtain 1.6kg of product, which was directly used in the next reaction.

[0028] Dissolve 1.6 kg of the product in the previous step in 5 liters of dichloromethane, add 1.5 kg of dibromohydantoin in batches, and react overnight at room temperature after adding, pour into 5 liters of ice water, extract the reaction with 10% sodium sulfite solution, and separate the liquids , conventional post-processing to obtain 1.1 kg of white solid product, which was directly used in the next reaction.

[0029] Dissolve 1.1 kg of the product in the previous step in 2 liters of methanol and 2 liters of DMF, add 2 kg of sodium m...

Embodiment 2

[0032] Add 5 liters of anhydrous methanol and 1.21 kg of S-phenylethylamine to a 10-liter four-necked flask, stir at room temperature for 15 minutes, then add 2.5 kg of trifluoroacetic anhydride dropwise, complete the addition, stir at room temperature, and concentrate after TLC detection , the obtained solid was washed with water, and vacuum-dried to obtain 2.1 kg of product, which was directly used in the next reaction.

[0033] Dissolve 2.1 kg of the product from the previous step in 5 liters of dichloromethane, add 1.5 kg of dibromohydantoin in batches, and react overnight at room temperature after adding, pour into 5 liters of ice water, extract the reaction with 10% sodium sulfite solution, and separate the liquids , conventional post-processing to obtain 1.5kg of white solid product, which was directly used in the next reaction.

[0034] Dissolve 1.5 kg of the product in the previous step in 2 liters of methanol and 2 liters of DMF, add 2 kg of sodium methoxide, 300 g o...

Embodiment 3

[0037] In a 10-liter four-neck flask, add 5 liters of anhydrous methanol and 1.21 kg of S-phenylethylamine, and after stirring at room temperature for 15 minutes, add 1.1 kg of acetic anhydride dropwise, complete the addition, stir at room temperature, concentrate after the TLC detection reaction, and obtain The solid was washed with water, and vacuum-dried to obtain 1.6kg of product, which was directly used in the next reaction.

[0038] Dissolve 1.6 kg of the product in the previous step in 5 liters of dichloromethane, add 1.3 kg of iodine in batches, and react overnight at room temperature after adding, pour into 5 liters of ice water, extract the reaction with 10% sodium sulfite solution, separate the liquids, and The white solid product 1.5kg obtained was directly used in the next reaction.

[0039] Dissolve 1.5 kg of the product in the previous step in 2 liters of methanol and 2 liters of DMF, add 2 kg of sodium methoxide, 300 g of cuprous cyanide, heat and reflux for 6 ...

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Abstract

The invention discloses a synthesis method of chiral p-methoxybenzylamine. The method uses chiral benzylamine as a starting material, and replaces a halogen atom with a methoxy group by protecting the amine group, para-halogenation, and Ullmann reaction. , and finally deprotected to obtain optical enantiopure chiral p-methoxybenzylamine. The method has low production cost, is easy to operate and is suitable for industrial production.

Description

Technical field: [0001] The invention relates to the field of synthesis of medical compounds, in particular to a synthesis method of chiral p-methoxybenzylamine. Background technique: [0002] Chiral benzylamine is a good class of reagents for resolution and construction of new chirality, and plays an important role in industry and pharmaceutical production. However, when it is used as a reagent for constructing a new chirality, it is often combined with the reaction substrate in the form of a covalent bond, and it must be dissociated before the final product is obtained (equivalent to the benzyl group on the deaminated group), which is to a certain extent There are difficulties. Commonly used hydrogenation methods require moderate or higher pressures, while metal reduction requires lower temperatures, which undoubtedly limit its application. Chiral p-methoxybenzylamine can be removed by oxidation (cerium ammonium nitrate or dichlorodicyanobenzoquinone), the reaction condi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/58C07C213/00
Inventor 沈鑫廖立新林复兴何晓杨继东詹华杏
Owner BAILING PHARMA SHANGHAI
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