Method for preparing chiral organoboron compound

A compound and organoboron technology, which is used in the application fields of functionalized chitosan-supported copper catalyzed preparation of chiral organoboron compounds, synthesis of delta-hydroxy compounds and drug molecules for the treatment of diabetes, which can solve the problem of harming human health and environmental pollution. Large, metal residue and other problems, to achieve the effect of easy method, wide application and low cost

Active Publication Date: 2019-12-20
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are also deficiencies in the above methods, such as the use of a monovalent copper homogeneous catalyst that is sensitive to water and air and has a high price, and the consumption is large, which will easily cause metal residues in the drug synthesis and seriously endanger human health; must Adding a strong base and using an organic solvent in the reaction system will cause great environmental pollution

Method used

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  • Method for preparing chiral organoboron compound
  • Method for preparing chiral organoboron compound
  • Method for preparing chiral organoboron compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] The preparation method of compound III-1, its steps are:

[0084]

[0085] A. Add functionalized chitosan-supported copper chloride catalytic material (HBCS@CuCl 2 ) 5mg and ligand L3 (3.0mg, 0.012mmol, 6mol%), add 2.5 mL of water, and stir at room temperature (20 or 22 or 24 or 25°C, the same below) for 1 hour;

[0086] B. To the above system, add starting material I-1 (58.9mg, 0.2mmol) and pinacol diborate (B 2 (pin) 2 ) (60.9mg, 0.24mmol);

[0087] C, the whole reaction system was stirred at room temperature for 12 hours to react;

[0088] D, after the reaction finishes, filter the whole reaction system, wash with tetrahydrofuran 3mL, directly add sodium perborate tetrahydrate (244mg, 0.8mmol) in the residue, and the whole system is stirred at room temperature for 4 hours;

[0089] E. Add ethyl acetate 3mL to the above system for dilution, extract with ethyl acetate (3×10mL), separate the organic phase, and use anhydrous Na 2 SO 4 Dry, filter and remove solv...

Embodiment 2

[0093] The preparation method of compound III-2, its steps are:

[0094]

[0095] A. Add functionalized chitosan-supported copper chloride catalytic material (HBCS@CuCl 2 ) 5mg and ligand L3 (3.0mg, 0.012mmol, 6mol%), add 2.5mL of water, and stir at room temperature (20 or 22 or 24 or 25°C, the same below) for 1 hour;

[0096] B, in above-mentioned system, successively add starting material I-2 (65.8mg, 0.2mmol) and biboronic acid pinacol ester (B 2 (pin) 2 ) (60.9mg, 0.24mmol);

[0097] C, the whole reaction system was stirred at room temperature for 12 hours to react;

[0098] D, after the reaction finishes, filter the whole reaction system, wash with tetrahydrofuran 3mL, directly add sodium perborate tetrahydrate (244mg, 0.8mmol) in the residue, and the whole system is stirred at room temperature for 4 hours;

[0099] E. Add 3 mL of ethyl acetate to the above system to dilute, extract with ethyl acetate (3×10 mL), separate the organic phase, and use anhydrous Na 2 S...

Embodiment 3

[0104] Preparation of compound III-3:

[0105]

[0106] A. Add functionalized chitosan-supported copper chloride catalytic material (HBCS@CuCl 2 ) 5mg and ligand L3 (3.0mg, 0.012mmol, 6mol%), add 2.5mL of water, and stir at room temperature (20 or 22 or 24 or 25°C, the same below) for 1 hour;

[0107] B, in above-mentioned system, successively add starting material I-3 (74.7mg, 0.2mmol) and biboronic acid pinacol ester (B 2 (pin) 2 ) (60.9mg, 0.24mmol);

[0108] C, the whole reaction system was stirred at room temperature for 12 hours to react;

[0109] D, after the reaction finishes, filter the whole reaction system, wash with tetrahydrofuran 3mL, directly add sodium perborate tetrahydrate (244mg, 0.8mmol) in the residue, and the whole system is stirred at room temperature for 4 hours;

[0110] E. Add 3 mL of ethyl acetate to the above system to dilute, extract with ethyl acetate (3×10 mL), separate the organic phase, and use anhydrous Na 2 SO 4 Dry, filter and remov...

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Abstract

The invention relates to the field of compound synthesis, in particular to a method for preparing chiral organoboron compound through catalysis of functionalized chitosan support copper, and further relates to application of the method for preparing the chiral organoboron compound through catalysis of functionalized chitosan support copper in synthesizing a delta-hydroxyl compound and diabetes treatment drug molecules. The functionalized chitosan support copper is adopted as a catalyst, bisdiboron is adopted as a reaction reagent, water is adopted as a solvent, sodium perborate tetrahydrate isadopted as an oxidant, boron addition reactions are selectively performed for substrates with different substituent groups respectively, and furthermore, the delta-hydroxyl compound is prepared through a continuous oxidation reaction.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a method for preparing chiral organoboron compounds by catalyzing functionalized chitosan-supported copper, and also relates to a method for preparing chiral organoboron compounds by catalyzing functionalized chitosan-supported copper Application of the method in the synthesis of delta-hydroxy compounds and drug molecules for the treatment of diabetes. Background technique [0002] So far, various organic and inorganic materials such as alumina, zeolites, polymers, and magnetic materials have been investigated as heterogeneous supports. Due to their instability at room temperature, high energy consumption, and time requirements during the preparation process, their applications are still greatly limited. Therefore, exploring new green, renewable, environmentally friendly, and low-cost heterogeneous catalytic materials has become an urgent and much-concerned issue. Polysacchari...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02B01J31/30
CPCC07F5/025B01J31/30B01J2231/323
Inventor 朱磊文蔚李博解魏鹏任李伟汪连生
Owner HUBEI ENG UNIV
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