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Process for synthesizing alpha-Schiff base derivatized beta-cyclodextrin

A synthesis method and cyclodextrin technology are applied in the field of synthesis of α-Schiff base derivatized β-cyclodextrin bonded silica chiral stationary phase, which can solve the problem of chiral separation and identification of samples with new polymer chiral columns. The problems of single species and single chiral column species can achieve the effect of recovery and recycling, simple synthesis route and high yield.

Inactive Publication Date: 2005-08-17
BEIJING INSTITUTE OF TECHNOLOGYGY
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Problems solved by technology

The molecular structure of this stationary phase is simple, the variety of samples identified during chiral separation is relatively narrow, and the application range is relatively narrow
In addition, although some polymer chiral stationary phase commercial columns, such as cyclodextrin commercial columns, have rich chiral environments, due to their complex molecular structures, commercial chiral columns have only a single variety, and the design of new polymer chiral columns and synthesis has become a bottleneck for chiral separations

Method used

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  • Process for synthesizing alpha-Schiff base derivatized beta-cyclodextrin
  • Process for synthesizing alpha-Schiff base derivatized beta-cyclodextrin
  • Process for synthesizing alpha-Schiff base derivatized beta-cyclodextrin

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Add 3g of cyclodextrin aldehyde and 45ml of pyridine to a 100ml reaction flask, turn on magnetic stirring, open the nitrogen protection valve, add 4.4ml of aniline solution, control the temperature of the external heating device to 25-30°C, stop heating and nitrogen protection after 4 days of reaction. The reaction liquid was dropped into acetone, cooled for 4 hours, and filtered with suction to obtain a solid which was washed twice with acetone to obtain a 6-aniline-β-cyclodextrin solid. The conversion rate of cyclodextrin aldehyde was 100%, and the yield of 6-aniline-β-cyclodextrin was 94%. Reaction conditions not mentioned in each comparative example and

[0018] Same as Example 1:

Embodiment 2

[0020] The conditions are the same as in Example 1, except that the addition of the aniline solution is changed to the addition of isopropylamine. The reaction result is: the conversion rate of cyclodextrin aldehyde is 100%, and the yield of 6-isopropylimine-β-cyclodextrin is 96%.

Embodiment 3

[0022] The conditions are the same as in Example 1, only the addition of the aniline solution is changed to the addition of R-(+)-phenylethylamine. The result of the reaction is: the conversion rate of cyclodextrin aldehyde is 100%, 6-R-(+)-phenylethyl The yield of β-cyclodextrin imine is 93%.

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Abstract

The present invention provides method of synthesizing new type alpha-Schiff base derived beta-cyclodextrin with beta-cyclodextrin aldehyde. The synthesis path has alpha-Schiff base radical introduced and beta-cyclodextrin aldehyde is made to react with various amine compounds, including aniline, isopropyl amine, R-(+)-phenyl ethylamine, S-(-)-phenyl ethylamine, R-binaphthalene phenol diamine, S-binaphthalene phenol diamine, S-binaphthalene phenol amine, etc. The present invention has simple synthesis path, high yield, simple operation and easy purification. The present invention is mainly used in chiral separation for research of amino acid, ferrocene amino compound, medicine, sulfur containing compound, etc. and may be also used in asymmetrical catalysis for the recovering and circular utilization of catalyst.

Description

Technical field [0001] The invention relates to a synthetic method for obtaining a novel α-Schiff base derivatized β-cyclodextrin bonded silica gel chiral stationary phase by using β-cyclodextrin aldehyde, and belongs to the field of chemical synthesis. Background technique [0002] In recent years, the rise of the chiral drug industry has led to the development of chiral separation. Chiral chromatography has been widely recognized by people because of its simple operation, fast separation speed and accurate analysis, and has become a hot spot in chiral separation research. In chiral chromatography, the chiral stationary phase is the key to separation, and it is often called the heart of chromatographic separation. Therefore, the research of different types of chiral stationary phases has far-reaching significance in promoting the development of chiral separation, promoting the continuous advancement of asymmetric synthesis and related disciplines, and driving economic developmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
Inventor 周智明方敏余从煊
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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