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Method for catalyzing reduction of iminodibenzyl carbon-based derivative

A technology for catalyzing iminodibenzylcarbonyl and derivatives, which is applied in the field of highly selective reduction of iminodibenzylcarbonyl derivatives and high efficiency, and can solve problems such as unfavorable practical application, excess, and large application limitations

Active Publication Date: 2019-10-25
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, chemists have conducted a lot of research on the reduction reaction of inert amides, and some successful reduction systems have emerged, such as: hydrogen reduction (Chem.Sci.2016, 7, 3432; Angew.Chem.Int.Ed. 2017,56,9381; ACSCatal.2018,8,8014), silane reduction (Chem.Rev.2014,114,5477; Chem.Rev.2019,119,2681), etc. Although the above methods have achieved certain success, most of them Involving excess reagents, long reaction time, harsh operating reaction conditions, especially the reduction reaction involves complex and expensive transition metal catalysts, resulting in large limitations in the application of this type of reaction, which is not conducive to practical application

Method used

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  • Method for catalyzing reduction of iminodibenzyl carbon-based derivative
  • Method for catalyzing reduction of iminodibenzyl carbon-based derivative
  • Method for catalyzing reduction of iminodibenzyl carbon-based derivative

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Experimental program
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Effect test

Embodiment 1

[0009] Embodiment 1, wherein amide substrate is as follows:

[0010] Amide substrate structure formula:

[0011]

[0012] Under argon atmosphere, sequentially add the formula amide substrate (0.5mmol), borane (1.5mmol, 3.0equiv.), THF (2mL), sodium triethylborohydride (4mol%) into a 10mL sealed tube, and Heat and stir in an oil bath at 80°C for 12 hours. After the reaction is complete, add 1M hydrochloric acid aqueous solution (4mL) to the reaction solution in an air environment, and stir at room temperature for 2 hours, extract and collect the organic phase, and separate the product by column chromatography , The yield is: 75%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 ,20°C) δ) δ 7.23-7.11 (m, 4H), 7.03-6.90 (m, 4H), 3.94-3.86 (m, 2H), 1.32-1.26 (m, 3H).

Embodiment 2

[0013] Embodiment 2, wherein amide substrate is as follows:

[0014] Amide substrate structure formula:

[0015]

[0016] Under argon atmosphere, sequentially add the formula amide substrate (0.5mmol), borane (1.5mmol, 3.0equiv.), THF (2mL), sodium triethylborohydride (4mol%) into a 10mL sealed tube, and Heat and stir in an oil bath at 80°C for 12 hours. After the reaction is complete, add 1M hydrochloric acid aqueous solution (4mL) to the reaction solution in an air environment, and stir at room temperature for 2 hours, extract and collect the organic phase, and separate the product by column chromatography , The yield is: 82%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 , 20°C) δ7.12 (m, 6H), 6.92 (m, 2H), 3.80 (m, 2H), 3.17 (m, 4H), 1.16 (t, J=8.0Hz, 3H).

Embodiment 3

[0017] Embodiment 3, wherein amide substrate is as follows:

[0018] Amide substrate structure formula:

[0019]

[0020] Under argon atmosphere, sequentially add the formula amide substrate (0.5mmol), borane (1.5mmol, 3.0equiv.), THF (2mL), sodium triethylborohydride (4mol%) into a 10mL sealed tube, and Heat and stir in an oil bath at 80°C for 12 hours. After the reaction is complete, add 1M hydrochloric acid aqueous solution (4mL) to the reaction solution in an air environment, and stir at room temperature for 2 hours, extract and collect the organic phase, and separate the product by column chromatography , The yield is: 72%. NMR data of the product: 1 H NMR (400MHz, CDCl 3 ,20℃)δ8.10(d,J=8.0Hz,2H),7.46(dd,J=8.0,8.0Hz,2H),7.41(d,J=8.0Hz,2H),7.23(dd,J= 8.0, 8.0Hz, 2H), 4.31 (t, J = 7.2Hz, 2H), 1.90-1.81 (m, 2H), 1.44-1.37 (m, 2H), 0.95 (t, J = 7.4Hz, 3H).

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Abstract

The invention relates to a method for catalyzing reduction of an iminodibenzyl carbon-based derivative. For the first time, non-transition metal compound sodium triethylborohydride is used as a catalyst, the reduction reaction of the iminodibenzyl carbon-based derivative with an inexpensive and easily available organoboron reagent can be catalyzed conveniently under mild conditions to prepare an iminodibenzyl product. Compared with a traditional method, the method generally has the advantages that the catalyst is cheap and easy to obtain, operation is convenient and reaction is safe. For the first time, the selective reduction reaction of the iminodibenzyl carbon-based derivative with the organoboron reagent is catalyzed by a non-transition metal catalyst, and a practical and novel reaction strategy is provided for the laboratory preparation or industrial production of the iminodibenzyl product.

Description

technical field [0001] The invention relates to a method for reducing iminodibenzylcarbyl derivatives with high efficiency and high selectivity. Background technique [0002] Iminodibenzyl compounds are important chemical intermediates and are widely used in the synthesis of drugs, natural products and polymers. The reduction reaction of iminodibenzylcarbonyl derivatives is an important method to expand organic amine compounds and explore new amine drug active molecules and natural products. In recent years, chemists have conducted a lot of research on the reduction reaction of inert amides, and some successful reduction systems have emerged, such as: hydrogen reduction (Chem.Sci.2016, 7, 3432; Angew.Chem.Int.Ed. 2017,56,9381; ACSCatal.2018,8,8014), silane reduction (Chem.Rev.2014,114,5477; Chem.Rev.2019,119,2681), etc. Although the above methods have achieved certain success, most of them Excessive amounts of reagents, long reaction time, and harsh operating conditions ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/22C07D223/22C07D209/86C07D265/38C07C211/55C07C209/50C07D219/02C07D209/88
CPCC07D279/22C07D223/22C07D209/86C07D265/38C07C211/55C07D219/02C07D209/88
Inventor 姚武冰陈滋双
Owner TAIZHOU UNIV