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Process for synthesizing chiral methoxybenzylamine

A technology of methoxybenzylamine and its synthesis method, which is applied in the field of synthesis of chiral p-methoxybenzylamine, and achieves the effects of easy operation, easy crystallization and purification, and favorable industrial production

Inactive Publication Date: 2009-06-24
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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  • Process for synthesizing chiral methoxybenzylamine
  • Process for synthesizing chiral methoxybenzylamine
  • Process for synthesizing chiral 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 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 1.5kg of white solid product, which was directly used in the next reaction.

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

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. 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.

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

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Abstract

The invention discloses a method for synthesizing chiral p-methoxy benzylamine. The method, with chiral benzylamine as original starting material, replaces halogen atom with methoxy by amidocyanogen protection, para position halogenating and Ullmann reaction; and finally, the protection is removed to obtain chiral p-methoxy benzylamine with pure optical enantiomorphism. The method is low in production cost, easy in operation and applicable to 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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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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