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Immobilized chiral catalyst, preparation method thereof, and synthesis method of chiral compounds

A chiral catalyst and solid-phase technology, which is applied in the preparation of organic compounds, physical/chemical process catalysts, ruthenium organic compounds, etc., can solve the problems of low stability, difficult recovery and reuse, and low conversion number. Achieve the effect of reducing synthesis cost, solving the risk of metal residue, and ensuring the catalytic conversion rate

Active Publication Date: 2020-02-28
GUANGXI ENANTIOTECH PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the research on asymmetric catalytic synthesis is still in its infancy, and there are still many problems to be solved urgently.
For example: Most chiral catalysts have low conversion numbers, low stability, and are difficult to recycle and reuse

Method used

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  • Immobilized chiral catalyst, preparation method thereof, and synthesis method of chiral compounds
  • Immobilized chiral catalyst, preparation method thereof, and synthesis method of chiral compounds
  • Immobilized chiral catalyst, preparation method thereof, and synthesis method of chiral compounds

Examples

Experimental program
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Effect test

preparation example Construction

[0052] The preparation method of the above-mentioned solid-phased chiral catalyst comprises the steps:

[0053] step one:

[0054]

[0055] 1) react raw material 1 and raw material 2 to obtain intermediate a;

[0056] 2) Substituting the intermediate a with the high molecular polymer R to obtain a dinitrogen ligand containing the high molecular polymer R;

[0057] Step two:

[0058] The transition metal compound, the bisphosphine ligand and the dinitrogen ligand described in step 1 are mixed in an organic solvent to perform a coordination reaction.

[0059] In one specific embodiment, in 2) of step 1, the temperature of the reaction is 60-90° C., and the time is 5-10 hours.

[0060] In one specific embodiment, in step 2, the conditions of the coordination reaction include: the reaction temperature is 20°C-120°C, and the time is 0.5h-20h. Preferably, the reaction temperature is 90°C-110°C, and the time is 0.5h-2h.

[0061] In one specific embodiment, in step 2, the molar ...

Embodiment 1

[0066] This embodiment is a kind of solid phase chiral catalyst (S)-1, its structure is as follows:

[0067]

[0068] Its preparation method steps are as follows:

[0069] Step 1: Synthesis of dinitrogen ligand:

[0070]

[0071] 1) Using dichloromethane as a solvent and EDC.HCl as a condensation agent, mix 1.1 mol of raw material 1 and 1.2 mol of raw material 2 at room temperature for condensation reaction for 5 hours. After the reaction is completed, add water to the reaction solution, separate and collect the organic phase , dry, and remove the solvent to obtain intermediate a;

[0072] 2) Mix 1.1 mol of intermediate a with 1.2 mol of polyethylene glycol (PEG), use DMF as a solvent, react at 80°C for 8 hours, and then filter with suction to collect the solid to obtain a dinitrogen complex containing polymer R. body;

[0073] Step 2: Synthesis of (S)-1

[0074]

[0075] Under the protection of argon, the [RuCl 2 (C 6 h 6 )] 2 8.2 mg and 20 mg of (S)-Diop (p...

Embodiment 2

[0077] This example is a solid-phase chiral catalyst (S)-2, the preparation method of which is similar to Example 1, except that the high molecular polymer used is cellulose. Its preparation method steps are as follows:

[0078] Step 1: Synthesis of dinitrogen ligand:

[0079]

[0080] 1) The preparation of intermediate a is the same as in Example 1;

[0081] 2) Mix 1.1 mol of intermediate a with 1.2 mol of hydroxypropylmethylcellulose (HPMC), use DMF as a solvent, react at 80°C for 8 hours, and then filter with suction to collect the solid, that is, the compound containing polymer R is obtained. Dinitrogen ligand;

[0082] Step 2: Synthesis of (S)-2

[0083]

[0084] Under the protection of argon, the [RuCl 2 (C 6 h 6 )] 2 8.2 mg and 20 mg of (S)-Diop (purchased from Aladdin) were suspended in 2 mL of DMF degassed with argon, and stirred at 100°C for 1 hour; the solvent was removed in vacuo at 50°C to obtain a brown solid; then, bis Nitrogen ligand 7.2 mg and 5...

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Abstract

The invention relates to an immobilized chiral catalyst, which has structural features shown in the description. The chiral catalyst has the advantages of high reaction selectivity and high stability,can be easily separated from the reaction product, does not have any metal residue, and can be recovered, and thus the reaction cost is reduced.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a solid-phase chiral catalyst, a preparation method thereof, and a synthesis method of chiral compounds. Background technique [0002] There are many methods for the synthesis of chiral drugs, and the most common ones are as follows: 1. Extraction from natural products, mainly extracting some important chiral substances from animals and plants; 2. Resolution of racemates, The acquisition of chiral drugs by splitting racemates is currently the most commonly used method; 3. Asymmetric catalytic synthesis, asymmetric catalytic synthesis mainly includes chemical asymmetric catalytic synthesis and biological asymmetric catalytic synthesis, by using catalysts Quantities of chiral raw materials are used to stereoselectively produce a large number of chiral products, and the chiral catalyst is recycled during the reaction to achieve the effect of chiral value-added or chiral a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24C07F15/00C07C29/00C07C33/22
CPCB01J31/2414B01J2231/641B01J2531/0213B01J2531/821C07C29/00C07F15/0053C07C33/22Y02P20/52
Inventor 徐亮蒙发明李彦雄毛波李苏泳罗凤玲郭俊
Owner GUANGXI ENANTIOTECH PHARM CO LTD
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