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A method for iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine to synthesize chiral exocyclic amine

A technology of chiral exocyclic amines and catalyzed quinoline, applied in chemical instruments and methods, catalytic reactions, physical/chemical process catalysts, etc., can solve problems such as strong coordination ability, low activity of aromatic amines, catalyst poisoning, etc., to achieve The effect of complete reaction, convenient preparation, high reactivity and enantioselectivity

Active Publication Date: 2017-03-15
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Claims
  • Application Information

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Problems solved by technology

However, there have been no reports on the asymmetric hydrogenation of aromatic amines, mainly due to the low activity and strong coordination ability of aromatic amines, which can easily lead to catalyst poisoning.

Method used

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  • A method for iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine to synthesize chiral exocyclic amine
  • A method for iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine to synthesize chiral exocyclic amine
  • A method for iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine to synthesize chiral exocyclic amine

Examples

Experimental program
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Embodiment 1

[0032] Example 1: Synthesis of various chiral exocyclic amine compounds by iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine

[0033] In a glove box filled with nitrogen, the reaction of (1,5-cyclooctadiene) iridium chloride dimer (0.0020 mmol) and chiral ligand (R)-DifluorPhos (0.0044 mmol) Add 1mL mixed solvent toluene / ditetrahydrofuran (v / v=3:1) into the bottle, stir the resulting solution at room temperature for 10-30 minutes, then transfer the prepared catalyst to another bottle containing the raw material quinoline-3 - In the reaction vials of amine (0.10 mmol) and iodine (0.0050 mmol), share 3 mL of solvent mixture solvent toluene / tetrahydrofuran (v / v=3:1). Stir at room temperature for 10-30 minutes, put the reaction bottle into a stainless steel autoclave, feed hydrogen gas at 200psi, and react at room temperature (or 45°C) for 18 hours. After the reaction, hydrogen gas was released slowly, the solvent was removed by a rotary evaporator, and the pure pro...

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Abstract

A method for synthesizing chiral exocyclic amine by iridium-catalyzed asymmetric hydrogenation of quinoline-3-amine, the catalytic system used is chiral diphosphorus complex of iridium. The reaction can be carried out under the following conditions, temperature: 25-70°C; solvent: a mixed solvent of toluene / tetrahydrofuran (V / V=3:1); pressure: 2-14 atmospheres; the ratio of substrate to catalyst is 25 / l; The catalyst is a complex of (1,5-cyclooctadiene) iridium chloride dimer and a chiral bisphosphine ligand. For quinoline-3-amine, the corresponding chiral exocyclic amine derivative can be obtained, and its enantiomeric excess value can reach 94%. The invention has the advantages of simple and practical operation, readily available raw materials, high enantioselectivity and good yield, and the reaction has green atom economy and is environmentally friendly.

Description

technical field [0001] The invention relates to a method for synthesizing chiral exocyclic amine by catalyzing the hydrogenation of quinoline-3-amine with high enantioselectivity in a homogeneous system of iridium. [0002] technical background [0003] Chiral exocyclic amines are a very important class of organic compounds. They are not only commonly used intermediates in many organic synthesis, but also can be used as catalysts to catalyze a series of asymmetric reactions. In addition, they also exist in numerous physiologically active molecules, including natural products and non-natural products. The three physiologically active molecules in the following formula 1 all contain chiral exocyclic amine structural units: [0004] [0005] It is precisely because of the importance of the chiral exocyclic amine structure in the field of medicine and synthetic chemistry that chemists have developed many methods to synthesize such compounds (Document 1: a) Xie, J.-H.; Zhu, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04B01J31/30
CPCB01J31/2295B01J2231/646B01J2531/827C07D401/04
Inventor 周永贵蔡先锋陈木旺
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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