A kind of preparation method of (r)-epinephrine

A technology of epinephrine and compound, applied in the field of preparation of (R)-epinephrine, to achieve the effects of high optical purity, mild reaction conditions and high optical yield

Active Publication Date: 2021-02-02
HENAN PURUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a new method for the preparation of (R)-adrenaline mainly aiming at the deficiency of the original technical method for obtaining single-configuration adrenaline

Method used

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  • A kind of preparation method of (r)-epinephrine
  • A kind of preparation method of (r)-epinephrine

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Experimental program
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Effect test

Embodiment 1

[0024] Such as figure 2 Shown, the preparation method of (R)-epinephrine of the present invention comprises the following steps:

[0025] 1) Add 11.0g (1mol) of catechol (compound 1) and 60.9g (1.1mol) of compound 2 into the reaction flask, then add 50mL of tetrahydrofuran and 21.2g of 50% aqueous sodium carbonate solution, and stir for 5 hours at room temperature Add 1N hydrochloric acid to the reaction solution to adjust the pH of the solution to 6-6.5, evaporate the tetrahydrofuran under reduced pressure, extract the residue with dichloromethane, 50 mL each time, extract three times, combine the dichloromethane layers, and wash with 50 mL of saturated sodium chloride aqueous solution Once, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to obtain 52.6 g of compound 3 with a yield of 90%.

[0026] 2) Put 52.6g (0.09mol) of compound 3, 10.2g (0.09mol) of chloroacetyl chloride and 6.9g (0.045mol) of phosphorus oxychloride into the reaction flask, rais...

Embodiment 2

[0031] The preparation method of (R)-epinephrine of the present invention comprises the following steps:

[0032] 1) Add catechol (compound 1) 11.0g (1mol) and compound 2 60.9g (1.1mol) into the reaction flask, then add acetonitrile 50mL and 50% sodium carbonate aqueous solution 21.2g, stir and react at room temperature for 5 hours Add 1N hydrochloric acid to the reaction solution to adjust the pH of the solution to 6-6.5, evaporate acetonitrile under reduced pressure, and extract the residue with dichloromethane, 50 mL each time, three times, combine the dichloromethane layers, and wash with 50 mL of saturated sodium chloride aqueous solution Once, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to obtain 352.3 g of the compound with a yield of 89.4%.

[0033] 2) Put 52.3g (0.09mol) of compound 3, 10.2g (0.09mol) of chloroacetyl chloride and 6.9g (0.045mol) of phosphorus oxychloride into the reaction flask, raise the temperature to 60±2°C for 3.5 hours...

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Abstract

The invention discloses a preparation method of (R)-epinephrine, which has the following advantages: (1) a new preparation process of (R)-epinephrine is provided; (2) the technological process is simple and the reaction conditions are mild , has a great application prospect; (3) the obtained product has high optical purity and high optical yield.

Description

technical field [0001] The invention belongs to the field of medicine preparation technology, and in particular relates to a preparation method of (R)-epinephrine. Background technique [0002] Adrenaline (adrenaline or epinephrine) is mainly used to treat cardiac arrest, bronchial asthma, anaphylactic shock, and also to treat urticaria, hay fever, and nasal mucosa or gingival bleeding. See its structure figure 1 . [0003] There is a chiral center in the epinephrine molecule, so there are two enantiomers R-adrenaline and S-adrenaline, and the main physiological activity is R-adrenaline. [0004] At present, the synthesis of epinephrine mainly includes split method and asymmetric synthesis method. [0005] There are two resolution methods, one is to use the corresponding α-halogenated acetophenone as raw material, after amination and reduction, and then carry out chemical resolution to obtain a single enantiomer product; the other is to use catechol and chlorine Acetyl ch...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/00C07C215/60C07H15/203C07H1/00
CPCC07B2200/07C07C213/00C07H1/00C07H15/203C07C215/60
Inventor 栗金梁乔爱红王慧郭永慧
Owner HENAN PURUI PHARMA
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