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Preparation method for alpha-amino ketone derivative

A technology of aminoketone and derivatives, which is applied in the field of preparation of α-aminoketone derivatives, and can solve the problems of too strong oxidation of reagents, serious side reactions, and low yield

Inactive Publication Date: 2012-07-18
SHANGHAI INST OF PHARMA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to overcome the reagent oxidizing property that is conventionally used in the method for oxidizing α-amino alcohol into α-amino ketone in the prior art is too strong, the side reaction is serious, the yield is not high, the environment is harmful However, it provides a mild oxidation method, which has cheap and easy-to-obtain reagents, mild reaction, high yield, little environmental pollution, convenient operation, and can be used in industrial production

Method used

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  • Preparation method for alpha-amino ketone derivative
  • Preparation method for alpha-amino ketone derivative
  • Preparation method for alpha-amino ketone derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0082] 4.042g (19.5mmol) of 2-(N-acetyl)methylamino-1-phenyl-1-propanol was dissolved in 30mL of ethyl acetate, and under stirring, 0.031g (0.2mmol, 0.01eq. ) 2,2,6,6-tetramethylpiperidine-1-oxyl radical, then slowly dropwise add 1.526g (6.58mmol, 0.34eq.) 10mL ethyl acetate solution of TCCA, after adding, stir at room temperature React for 30 minutes. After the reaction was completed, it was washed twice with 30 mL of saturated sodium bisulfite solution and 30 mL of distilled water successively, and concentrated. 3.888 g of the concentrate was obtained. The calculated yield was 97.12%. After identification by HPLC, it was known that the product was 2-(N-acetyl)methylamino-1-phenyl-1-propanone, and the HPLC purity was 99.5%.

Embodiment 2

[0084] 4.501g (21.7mmol) of 2-(N-acetyl)methylamino-1-phenyl-1-propanol was dissolved in 30mL of toluene, and under stirring, 0.036g (0.23mmol, 0.01eq.)2 was added to the system , 2,6,6-tetramethylpiperidine-1-oxyl radical, then slowly dropwise add 1.543g (6.65mmol, 0.33eq.) 10mL toluene solution of TCCA, after adding, stir and react at room temperature for 30 minutes . After the reaction was completed, it was washed twice with 30 mL of saturated sodium bisulfite solution and 30 mL of distilled water successively, and concentrated. 3.748 g of the concentrate was obtained. The calculated yield was 84.08%. The HPLC purity of the product in the reaction solution was 94.37%.

Embodiment 3

[0086] 0.503g (2.4mmol) of 2-(N-acetyl)methylamino-1-phenyl-1-propanol was dissolved in 10mL of ethyl acetate, and under stirring, 0.004g (0.02mmol, 0.01eq. ) 2,2,6,6-tetramethylpiperidine-1-oxygen free radical, then slowly dropwise add 0.188g (0.8mmol, 0.33eq.) 5mL ethyl acetate solution of TCCA, after adding, at 40°C The reaction was stirred for 30 minutes. After the reaction was completed, it was washed twice with 15 mL of saturated sodium bisulfite solution and 15 mL of distilled water successively, and concentrated. 0.483 g of the concentrate was obtained. The calculated yield was 96.97%. The HPLC purity of the product in the reaction solution was 98.2%.

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Abstract

The invention discloses a preparation method for an alpha-amino ketone derivative as represented by formula II. The derivative is prepared by subjecting a compound as represented by formula I to a reaction in an organic solvent under the action of trichloroisocyanuric acid and an oxidation catalyst or subjecting the compound as represented by formula I to a reaction in an organic solvent with a pH value of 8 to 11 under the action of an oxidizing agent, an oxidation catalyst, a pH conditioning agent and a phase-transfer catalyst, wherein, R1, R2 and R3 are, independently, lower alkyl groups, aryl groups, aryl-substituted lower alkyl groups, lower alkoxy groups, aryl-substituted lower alkoxy groups, carboxyl-substituted lower alkyl groups or carbonyl groups connected with lower alkyl groups, and R4 is a carbonyl group connected with a lower alkyl group, a carbonyl group connected with an aryl group or a carbonyl group connected with a phenyl-substituted lower alkyl group. The preparation method provided in the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, small pollution to the environment and a high conversion rate of the raw material and is beneficial for industrial large-scale production.

Description

technical field [0001] The present invention relates to a preparation method of α-aminoketone derivatives. Background technique [0002] Pseudoephedrine is the main functional ingredient of various anti-cold medicines. Years of clinical practice have shown that it is a safe and effective medicine, and it is widely used at home and abroad. [0003] In the recrystallization mother liquor of pseudoephedrine production process, only contain about 5% (1S, 2S) type pseudoephedrine, about 95% are its (1R, 2R) type isomers. How to convert unwanted (1R, 2R) isomers into useful (1S, 2S) configurations is an important issue to be solved in industrial production. The conventional transformation method is realized through a series of operation steps such as oxidation, heating racemization, reduction, hydroxyl acylation, isomerization, hydrolysis, addition of alkali, and resolution. Among them, the choice of oxidation method is the most critical part. [0004] The reagents commonly use...

Claims

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Application Information

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IPC IPC(8): C07C233/31C07C231/12
Inventor 龚丹萍黄成军姜碧波
Owner SHANGHAI INST OF PHARMA IND
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