Preparation method of terbutaline

A technology for terbutaline and a compound, which is applied in the field of preparation of terbutaline, can solve the problems of expensive and unobtainable raw materials, lack of economy, long synthesis route and the like, and achieves easy control of the reaction process, shortened reaction steps and mild reaction conditions. Effect

Pending Publication Date: 2021-10-01
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Some of the above seven routes have long synthetic routes and require hydroxyl protection and deprotection reactions, and the steps are cumbersome; some require catalytic hydrogenation reactions, which are unsafe; some require bromination reactions, which are difficult to control; sex

Method used

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  • Preparation method of terbutaline
  • Preparation method of terbutaline
  • Preparation method of terbutaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1 Preparation of compound 1b (3,5-dihydroxybenzeneboronic acid pinacol ester)

Embodiment 1-1

[0065]

[0066] Under nitrogen protection, 19.0g 5-bromoresorcinol, 28.0g biboronic acid pinacol ester, 30.0g potassium acetate and 2.2g Pd(dppf)Cl were mixed 2 Dissolve in 150 mL of 1,4-dioxane, heat to 100 °C, and monitor by TLC to detect no 5-bromoresorcinol. The mixture was cooled to room temperature, diluted with toluene, filtered to remove insolubles, the filtrate was washed with an equal volume of water, the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness to obtain 21.1 g of compound 1b with a yield of 89.0%, HPLC purity 95.8%.

Embodiment 1-2

[0068]

[0069] Under nitrogen protection, 14.0g 5-chlororesorcinol, 28.0g biboronic acid pinacol ester, 25.0g sodium acetate and 2.2g Pd(dppf)Cl were mixed 2 Dissolved in 150 mL DMSO, heated to 120°C, and monitored by TLC for the absence of 5-chlororesorcinol. It was cooled to room temperature, diluted with toluene, filtered to remove insolubles, the filtrate was washed with an equal volume of water, the organic phase was separated, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness to obtain 19.5 g of compound 1b with a yield of 82.3%. HPLC purity 95.6%.

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Abstract

The invention provides a preparation method of terbutaline, and relates to the technical field of chemical synthesis. The preparation method of terbutaline comprises the following steps: (a) carrying out Suzuki reaction on a compound 1 and halogenated ethylene oxide to obtain a compound 2; and (b) reacting the compound 2 with tert-butylamine to obtain terbutaline. The Suzuki reaction is creatively applied to the preparation of terbutaline, so that the reaction steps are greatly shortened, the processes of bromination reaction, protection group loading on hydroxyl and deprotection are avoided, catalytic hydrogenation is not needed, the reaction conditions are mild, the reaction process is easy to control, and the safety coefficient is high. Raw materials are simple and easy to obtain, and the industrialization cost is saved. The product yield is high, the purity is high, and a process route capable of industrially producing a product with higher quality is provided.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of terbutaline. Background technique [0002] Terbutaline sulfate, chemically named α-[(tert-butylamino)methyl]-3,5-dihydroxyphenylmethanol sulfate, is used to treat bronchial asthma, asthmatic bronchitis and emphysema. β2-receptor agonists have a bronchodilator effect. It is highly selective to bronchial smooth muscle, has little excitatory effect on the heart, and has no central effect. For bronchial asthma, asthmatic bronchitis, obstructive emphysema and other lung diseases with bronchospasm. It is especially suitable for asthma patients with cardiovascular diseases such as hypertension and coronary heart disease. [0003] The synthetic method of the terbutaline reported in the literature mainly contains following several kinds at present: [0004] 1. Using 3,5-dihydroxybenzoic acid as raw material, terbutaline sulfate was prepared through e...

Claims

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Application Information

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IPC IPC(8): C07C215/60C07C213/04C07C213/00
CPCC07C213/04C07C213/00C07D303/14C07D301/00C07C215/60Y02P20/55
Inventor 李强张静王敏
Owner TIANJIN PHARMA GROUP CORP
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