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Catalyst, method for synthesizing (S)-octopamine and method for synthesizing (S)-N-trans-feruloyloctopamine

A synthesis method and catalyst technology, which are applied in the synthesis field of -N-trans-feruloyl-desmethylsypheline, can solve the problems of high requirements for synthesis conditions, complicated operations, numerous steps, etc., and improve synthesis efficiency and yield. high efficiency, high catalytic efficiency, and simple steps

Active Publication Date: 2011-05-18
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

This method not only has many steps and cumbersome operation, but also uses NaN 3 Toxic and explosive substances, which require high synthesis conditions

Method used

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  • Catalyst, method for synthesizing (S)-octopamine and method for synthesizing (S)-N-trans-feruloyloctopamine
  • Catalyst, method for synthesizing (S)-octopamine and method for synthesizing (S)-N-trans-feruloyloctopamine
  • Catalyst, method for synthesizing (S)-octopamine and method for synthesizing (S)-N-trans-feruloyloctopamine

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[0085] The present invention also provides a kind of synthetic method of (S)-octopamine, comprising:

[0086] a), under the action of the catalyst described in the above technical scheme, p-Hydroxybenzaldehyde and nitromethane react to generate (S)-octopamine precursor;

[0087] b) Under the action of a palladium-carbon catalyst, the (S)-octopamine precursor undergoes a hydrogenation reduction reaction with hydrogen to generate (S)-octopamine.

[0088] The catalyst described in the above technical scheme catalyzes the reaction between p-hydroxybenzaldehyde and nitromethane to generate (S)-octopamine precursor, and the reaction formula is as follows:

[0089]

[0090] The precursor of (S)-octopamine is (S)-1-(4-hydroxyphenyl)-2-nitroethanol.

[0091] In the reaction of generating (S)-octopamine precursor, the molar ratio of the ligands in the p-hydroxybenzaldehyde, nitromethane and catalyst is preferably 1:2~20:0.01~0.3, more preferably 1: 5-15:0.05-0.3, most preferably 1:...

Embodiment 1

[0107] Under argon protection, 2.533g (10mmol) of commercially available (S)-diphenylprolinol, 1.901g (10mmol) of commercially available 2-hydroxy-3-trifluoromethyl- Benzaldehyde, 20mL ethanol and a stirring magnet, stir at room temperature, track the reaction until the amine disappears, add 378.3mg (10mmol) NaBH 4 , After stirring at room temperature for 24h, the reaction was quenched by adding 1mol / L HCl, and then saturated NaHCO 3 The reaction mixture was neutralized to a pH value of 7, extracted 3 times with 20 mL of ethyl acetate, and the resulting organic phase was dried over anhydrous sodium sulfate, spin-dried and passed through a silica gel column, and the mobile phase was petroleum with a volume ratio of 1:6. ether and ethyl acetate to give 3.42 g of product in 80% yield, [α] D 25 +91.0 (c 1.18, CH 2 Cl 2 ).

[0108] Carry out nuclear magnetic resonance to described product, the result sees figure 1 and figure 2 , figure 1 The H NMR spectrum of the ligand pr...

Embodiment 2

[0110] Under argon protection, add 2.533g (10mmol) commercially available (S)-diphenylprolinol, 1.362g (10mmol) commercially available 2-hydroxyl-3-methyl-benzaldehyde to a 50mL round bottom bottle , 20mL ethanol and a stirring magnet, stirred at room temperature, tracked the reaction until the amine disappeared, added 378.3mg (10mmol) NaBH 4 , After stirring at room temperature for 24h, the reaction was quenched by adding 1mol / L HCl, and then saturated NaHCO 3 The reaction mixture was neutralized to a pH value of 7, extracted 3 times with 20 mL of ethyl acetate, and the resulting organic phase was dried over anhydrous sodium sulfate, spin-dried and passed through a silica gel column, and the mobile phase was petroleum with a volume ratio of 1:8. ether and ethyl acetate to give 2.801 g of product, yield 75%, [α] D 25 +61.2 (c 0.92, CH 2 Cl 2 ).

[0111] Carry out nuclear magnetic resonance to described product, the result sees image 3 and Figure 4 , image 3 The H NM...

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Abstract

The invention provides a catalyst, which comprises a ligand, a cupric compound, an alkaline inorganic compound, a phenol compound and tetrabutyl ammonium bromide, wherein the ligand has a structure shown in a formula (I), wherein R refers to alkyl or halogenated alkyl. The invention provides a method for synthesizing (S)-octopamine, which comprises the following steps of: a) performing reaction on hydroxy benzaldehyde and nitromethane in the presence of the catalyst in the technical scheme to generate an (S)-octopamine precursor; and b) performing hydrogenation reduction reaction on the (S)-octopamine precursor and hydrogen in the presence of a palladium carbon catalyst to generate the (S)-octopamine. The invention also provides a method for synthesizing (S)-N-trans-feruloyloctopamine, which comprises the following step of: performing amidation reaction on the (S)-octopamine and ferulic acid to generate the (S)-N-trans-feruloyloctopamine.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a catalyst, a method for synthesizing (S)-octopamine and a method for synthesizing (S)-N-trans-feruloyl norsynephrine. Background technique [0002] N-trans-feruloyl norsynephrine is a kind of phenolic cyclic amide compound, which exists in plants such as eggplant root, Polygonatum odoratum, garlic, wolfberry and so on, which can be used as traditional Chinese medicine, and has anti-oxidation, anti-aging, antibacterial and other effects . N-trans-feruloyl norsynephrine is a chiral compound, both reported in Journal of the American Chemical Society (Journal of the American Chemical Society, 2003, 125, 14672) and ChemBioChem in Germany (ChemBioChem, 2006, 7, 1916) (S)-N-trans-feruloyl norsynephrine has anti-cancer effect, and confirmed that its ability to kill cancerous white blood cells is better than its enantiomer (R)-N-trans-feruloyl Norsynephrine is stronger. [0003] (S)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/26B01J31/22C07C215/60C07C213/02C07C235/34C07C231/02C07C201/12
Inventor 汪志勇赖国银郭锋锋查正根
Owner UNIV OF SCI & TECH OF CHINA
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