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Preparation method of chiral beta-hydroxy acid ester compound

A technology of hydroxycarboxylates and compounds, which is applied in the field of preparing chiral β-hydroxycarboxylate compounds, can solve the problems of sodium cyanide wastewater, environmental pollution, and low rectification yield, and achieve mild hydrogenation reaction conditions and applicable The effect of wide range and low environmental pollution

Inactive Publication Date: 2019-10-15
SHANGHAI SHINE HIGH INT TRADE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The raw material of this method is cheap, and the reaction is mature, but the rectification yield is not high, the product is difficult to reach the required purity, and a large amount of sodium cyanide waste water is produced in the production process, which causes serious pollution to the environment

Method used

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  • Preparation method of chiral beta-hydroxy acid ester compound
  • Preparation method of chiral beta-hydroxy acid ester compound
  • Preparation method of chiral beta-hydroxy acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In this example, under nitrogen protection, dichlorophenylruthenium dimer (0.0025mmol, 0.5mol%), chiral phosphine-aminophosphine ligand (0.0055mmol, 1.1mol%) and potassium tert-butoxide (0.025mmol, 5.0mol%) was dissolved in ethanol (1.0mL), stirred at room temperature for 10 minutes, added a solution of the substrate ethyl phenylacetoacetate (0.5mmol) in ethanol (1.0mL), and placed it in an autoclave , replaced by hydrogen for 3 times, then introduced hydrogen to 20 atmospheres, and reacted at 100°C for 24 hours. Slowly release hydrogen gas, remove the solvent and separate with a silica gel column to obtain the product 3-hydroxyl-3-phenylpropanoic acid ethyl ester.

[0037] Wherein, the chiral phosphine-aminophosphine ligand is:

[0038]

[0039] The reaction equation is as follows:

[0040]

[0041] The yield and selectivity of the product were detected by chiral high performance liquid chromatography. The yield of the product ethyl 3-hydroxy-3-phenylpropionat...

Embodiment 2

[0045]In this example, under nitrogen protection, dichlorophenylruthenium dimer (0.0025mmol, 0.5mol%), chiral phosphine-aminophosphine ligand (0.0055mmol, 1.1mol%) and potassium hydroxide ( 0.025mmol, 5.0mol%) was dissolved in ethanol (1.0mL), stirred at room temperature for 10 minutes, and a solution of substrate ethyl phenylacetoacetate (0.5mmol) in ethanol (1.0mL) was added, and it was placed in an autoclave, Hydrogen was replaced 3 times, and then hydrogen was introduced to 20 atmospheres, and the reaction was carried out at 100°C for 24 hours. Slowly release hydrogen gas, remove the solvent and separate with a silica gel column to obtain the product 3-hydroxyl-3-phenylpropanoic acid ethyl ester.

[0046] Wherein, the chiral phosphine-aminophosphine ligand is:

[0047]

[0048] The yield and selectivity of the product were detected by chiral high performance liquid chromatography. The yield of the obtained product ethyl 3-hydroxy-3-phenylpropionate was 95%, and the se...

Embodiment 3

[0051] In this example, under nitrogen protection, dichlorophenylruthenium dimer (0.0025mmol, 0.5mol%), chiral phosphine-aminophosphine ligand (0.0055mmol, 1.1mol%) and potassium tert-butoxide (0.025mmol, 5.0mol%) was dissolved in ethanol (1.0mL), stirred at room temperature for 10 minutes, added a solution of the substrate ethyl phenylacetoacetate (0.5mmol) in ethanol (1.0mL), and placed it in an autoclave , replaced by hydrogen for 3 times, then introduced hydrogen to 60 atmospheres, and reacted at 100°C for 24 hours. Slowly release hydrogen gas, remove the solvent and separate with a silica gel column to obtain the product 3-hydroxyl-3-phenylpropanoic acid ethyl ester.

[0052] Wherein, the chiral phosphine-aminophosphine ligand is:

[0053]

[0054] The yield and selectivity of the product were detected by chiral high performance liquid chromatography. The yield of the obtained product ethyl 3-hydroxy-3-phenylpropionate was 96%, and the selectivity was 94%.

[0055] ...

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Abstract

The invention discloses a preparation method of a chiral beta-hydroxy carboxylic ester compound. The method comprises the following steps: dissolving a dichlorophenyl ruthenium dimer, a ligand and analkaline additive in a solvent under the protection of inert gas, and stirring at room temperature to generate a catalyst in situ; dissolving the substrate, beta-carbonyl carboxylic ester, into the solvent, adding the prepared catalyst, and feeding hydrogen to carry out asymmetric catalytic hydrogenation reaction on the beta-carbonyl carboxylic ester, wherein the reaction conditions are as follows: the pressure is 10-100 bar, the reaction temperature is 0-200 DEG C, and the reaction time is 12-48 hours. The method has the advantages of high reaction activity and selectivity, mild hydrogenationreaction conditions, wide substrate application range and small environmental pollution in the reaction process, and is suitable for various beta-carbonyl carboxylic esters.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, in particular to a method for preparing chiral β-hydroxycarboxylate compounds. Background technique [0002] Chiral β-hydroxy acid ester compounds are important intermediates in organic synthesis and can be used to prepare various natural and non-natural compounds with biological activity. Among them, L-carnitine, also known as vitamin BT, transliterated L-carnitine, is a compound naturally occurring in human cells, which promotes the conversion of fat into energy-like amino acids. Chiral epichlorohydrin is often used as a starting point in industry. The chemical synthesis method of raw material, reaction equation is as follows: [0003] [0004] Chemical Synthesis of Chiral Epichlorohydrin as Starting Material [0005] The method is simple, the raw materials are cheap, and the yield is good, but the production process requires a large amount of sodium cyanide aqueous sol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31B01J31/24C07C69/732C07C69/675
CPCB01J31/2409B01J2231/643B01J2531/821C07B2200/07C07C67/31C07C69/732C07C69/675
Inventor 胡信虎呼延旺
Owner SHANGHAI SHINE HIGH INT TRADE CO LTD
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