A kind of method of synthesizing α-amino boron compound

A boron compound and amino technology, which is applied in the field of synthesizing α-amino boron compounds, can solve problems such as poor functional group compatibility, and achieve the effects of strong functional group compatibility, safe reaction operation, and good atom economy

Active Publication Date: 2020-04-28
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest problem of this type of method is that the basic use of functional group-guided regulation of chirality, and partial use of ligand regulation, chirality control and substrate applicability have certain limitations; in addition, the poor compatibility of some functional groups is also a practical problem
However, there is no direct synthesis of sp using alkyne ammonia as a raw material. 3 Report on α-Aminoboron Compounds

Method used

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  • A kind of method of synthesizing α-amino boron compound
  • A kind of method of synthesizing α-amino boron compound
  • A kind of method of synthesizing α-amino boron compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) Add 0.3 mmol of N-methyl-N-(phenylethynyl) p-toluenesulfonamide, 0.36 mmol of pinacol diborate, 0.03 mmol of cuprous chloride and 0.036 mmol of Mole of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.045 mmol of sodium tert-butoxide, add 2 mL of toluene as a solvent, stir and react at room temperature for 12 hours, then filter, The solvent was spin-dried to obtain a crude product.

[0035] (2) After adding 3 mL of ethyl acetate to the crude product of step (1), transfer it to the autoclave, add 0.03 mmol of palladium / carbon, and then feed hydrogen at 20 atmospheres, and stir at a temperature of 60 degrees for 12 After 1 hour, filter, spin dry, add 2mL of petroleum ether to dissolve, take the petroleum ether layer, repeat three times, combine the petroleum ether layer, remove the solvent by rotary evaporation under reduced pressure, and then passivate through the previously prepared silica gel and water mass ratio of 1:0.35 The target product was obtained by separa...

Embodiment 2

[0044] (1) In a 25mL test tube, add 0.3 mmol of N-methyl-N-(phenylethynyl) methanesulfonamide, 0.36 mmol of pinacol biborate, 0.03 mmol of cuprous chloride and 0.036 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.045 mmol of sodium tert-butoxide, adding 2 mL of toluene as a solvent, stirring and reacting at room temperature for 12 hours, filtering, spinning The solvent was dried to obtain the crude product.

[0045] (2) After adding 3 mL of ethyl acetate to the crude product of step (1), transfer it to the autoclave, add 0.03 mmol of palladium / carbon, and then feed hydrogen at 20 atmospheres, and stir at a temperature of 60 degrees for 12 After 1 hour, filter, spin dry, add 2mL of petroleum ether to dissolve, take the petroleum ether layer, repeat three times, combine the petroleum ether layer, remove the solvent by rotary evaporation under reduced pressure, and then passivate through the previously prepared silica gel and water mass ratio of 1:0.35 Silica gel colum...

Embodiment 3

[0054] (1) Add 0.3 mmol of 3-(phenylethynyl) oxazolidin-2-one, 0.36 mmol of pinacol biborate, 0.03 mmol of cuprous chloride and 0.036 mmol of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, 0.045 mmol of sodium tert-butoxide, add 2 mL of toluene as a solvent, stir and react at room temperature for 12 hours, filter and spin dry solvent, the crude product was obtained.

[0055] (2) After adding 3 mL of ethyl acetate to the crude product of step (1), transfer it to the autoclave, add 0.03 mmol of palladium / carbon, and then feed hydrogen at 20 atmospheres, and stir at a temperature of 60 degrees for 12 After 1 hour, filter, spin dry, add 2mL of petroleum ether to dissolve, take the petroleum ether layer, repeat three times, combine the petroleum ether layer, remove the solvent by rotary evaporation under reduced pressure, and then passivate through the previously prepared silica gel and water mass ratio of 1:0.35 Silica gel column separation and purification to obtain the target p...

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a method for synthesizing an alpha-amino boron compound. The method comprises the following steps: alkynyl amine, B2Pin2, a base, a ligand, a copper salt catalyst and an organic solvent are added to a reactor and subjected to a stirring reaction at room temperature for 6-12 h, cooling is performed after the reaction, areaction liquid is filtered, the solvent is removed by evaporation, and a crude product is obtained; the obtained crude product is mixed with a reaction solvent, the mixture is fed into a pressure reactor, a catalyst is added, hydrogen under certain pressure is introduced, the substances are subjected to a stirring reaction at 40-80 DEG C for 6-12 h, cooling is performed after the reaction, separation and purification are performed on a product, and the alpha-amino boron compound is obtained. The method has the advantages of simple and easily available raw materials, safe reaction operation,environment-friendly reaction process, high substrate applicability, highly compatible functional groups and good atom economy, and is extensively applied to pesticides and medicines.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing α-aminoboron compounds. Background technique [0002] α-Aminoboron compounds have a wide range of medicinal activities and are important structural units of many bioactive molecules and drug molecules, such as Ixazomib and Bortezomib. For this reason, scientific research workers have conducted a lot of research on this kind of compound, and found that α-amino boron compounds have important functions such as antibacterial and antitumor. Although such compounds have such important applications, unfortunately there are not many synthetic methods for α-aminoboron compounds. [0003] The traditional synthetic method of constructing α-aminoboron compound generally will use imine and biboronate (S.Kawamorita, T.Miyazaki, T.Iwai, H.Ohmiya, M.Sawamura, Bioorg.J.Am.Chem. Soc.134(2012), 12924-12927; M.A.Beenen, C.An, J.A.Ellman J.Am.Chem.Soc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 江焕峰朱忠智伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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