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Method for synthesizing alpha-amino ketone from ketone and imine

An amino ketone, imine technology, applied in the preparation of sulfonic acid amides, organic chemistry and other directions, to achieve the effect of simple experimental steps, a wide range of substrates, and mild conditions

Inactive Publication Date: 2014-03-12
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In terms of synthetic methods, the oxidative C-N bond coupling reaction between the nitrogen source N-H bond and the ketone α-position sp3 hybridized C-H bond is one-step construction of the C-N bond, which is the simplest and most effective method for the synthesis of α-amino ketones. However, such methods are rarely reported

Method used

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  • Method for synthesizing alpha-amino ketone from ketone and imine
  • Method for synthesizing alpha-amino ketone from ketone and imine
  • Method for synthesizing alpha-amino ketone from ketone and imine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add ethyl acetate as an organic solvent (3.0 ml) into the pressure-resistant tube, add 1 times the amount of saccharin to fully dissolve (54.9 mg, 0.30 mmol), and then add 5 times the amount of acetone (0.111 liters, 1.50 mmol), 0.20 times the amount of catalyst tetrabutylammonium iodide (22.20 mg, 0.06 mmol), 2 times the amount of oxidant tert-butanol peroxide (0.109 ml, 0.60 mmol), and seal the pressure-resistant tube , heating at 130 o C, stirred for 3 hours (the above-mentioned dosage ratios are molar ratios, and can be scaled up in proportion); after the reaction, the system was cooled to room temperature, and then passed through methylene chloride (CH 2 Cl 2 ) extraction (15ml×3 times); the obtained organic phase was removed on a rotary evaporator to remove the organic solvent; the obtained solid was separated and purified by column chromatography to obtain a white solid with a yield of 91%. The reaction can be expressed by the following equation:

[0023]

Embodiment 2

[0025] Add ethyl acetate as an organic solvent (3.0 ml) into the pressure-resistant tube, add 1 times the amount of saccharin to fully dissolve (54.9 mg, 0.3 mmol), and then add 5 times the amount of acetone (0.111 liters, 1.5 mmol), 0.15 times the amount of catalyst tetrabutylammonium iodide (16.61 mg, 0.045 mmol), 2 times the amount of oxidant tert-butanol peroxide (0.109 ml, 0.6 mmol), and seal the pressure-resistant tube , heating at 130 o C, stirred for 3 hours (the above-mentioned dosage ratios are molar ratios, and can be scaled up in proportion); after the reaction, the system was cooled to room temperature, and then passed through methylene chloride (CH 2 Cl 2 ) extraction (15ml×3 times); the obtained organic phase was removed on a rotary evaporator to remove the organic solvent; the obtained solid was separated and purified by column chromatography to obtain a white solid with a yield of 89%. The reaction can be expressed by the following equation:

[0026]

Embodiment 3

[0028] Add ethyl acetate as an organic solvent (3.0 ml) into the pressure-resistant tube, add 1 times the amount of saccharin to fully dissolve (54.9 mg, 0.30 mmol), and then add 5 times the amount of acetone (0.111 liters, 1.50 mmol), 0.20 times the amount of catalyst tetrabutylammonium iodide (22.20 mg, 0.06 mmol), 1.5 times the amount of oxidant tert-butanol peroxide (0.081 ml, 0.45 mmol), and seal the pressure-resistant tube , heating at 130 o C, stirred for 3 hours (the above-mentioned dosage ratios are molar ratios, and can be scaled up in proportion); after the reaction, the system was cooled to room temperature, and then passed through methylene chloride (CH 2 Cl 2 ) extraction (15ml×3 times); the obtained organic phase was removed on a rotary evaporator to remove the organic solvent; the obtained solid was separated and purified by column chromatography to obtain a white solid with a yield of 85%. The reaction can be expressed by the following equation:

[0029] ...

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Abstract

The invention discloses a method for synthesizing alpha-amino ketone from ketone and imine, and belongs to the technical field of chemical organic synthesis. The method comprises the following steps: adding imine into an organic solvent, sufficiently dissolving so as to obtain an imine solution, further respectively adding ketone, a catalyst tetrabutyl ammonium iodide and an oxidant tert-butyl hydroperoxide into the solution, sealing up a tube opening, heating to be 130 DEG C, stirring for 3 hours, cooling down the system to be the room temperature after the reaction is ended, extracting by using dichloromethane and removing the solvent of on organic phase so as to obtain alpha-amino ketone. By adopting the method, defects in the conventional method for synthesizing alpha-amino ketone by electrophilic amination and nucleophilic amination are overcome, direct amination of alpha-position of a simple ketone compound such as acetone is achieved, a C-N bond is generated through oxidative coupling reaction between a N-H bond and a C-H bond at one step, and the alpha-position of a ketone substrate does not need to be prefunctionalized, so that the experiment steps are simple, the condition is gentle, the reagents are cheap, and the range of the substrate is wide; the method is applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical organic synthesis, and relates to a method for synthesizing α-aminoketone. Background technique [0002] α-aminoketones are a class of organic molecules that are very important in the field of biology, such as cysteine ​​protease inhibitors (" J. Am. Chem. Soc." 1999, 121 , 9907. ) is the polymeric α-amino ketone. In addition, compounds such as α-amino ketones can also synthesize various heterocyclic structures ( "J. Org. Chem." 1994, 59 , 1589. "Tetrahedron Lett." 2003, 44 , 5965. "Org. Lett." 2004, 6 , 843) and 1,2-diaminoalcohols ( "Chem.Re V .》 1996, 96 , 835.) useful precursors. In terms of synthetic methods, the oxidative C-N bond coupling reaction between the nitrogen source N-H bond and the ketone α-position sp3 hybridized C-H bond is one-step construction of the C-N bond, which is the simplest and most effective method for the synthesis of α-amino ketones. However, such...

Claims

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Application Information

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IPC IPC(8): C07D275/04C07D209/48C07D207/404C07D275/06C07C311/49C07C303/36
CPCC07C303/40C07D207/404C07D209/48C07D275/06C07C311/48
Inventor 张茜张前李燕吕允贺
Owner NORTHEAST NORMAL UNIVERSITY
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