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Preparing method of dextromethorphan impurity 17-methylmorphinan-3-alcohol enantiomer (DXM-B)

A technology of methylmorphinan and enantiomer, which is applied in the field of preparation of dextromethorphan impurity 17-methylmorphinan-3-ol enantiomer, can solve the problem of DXM-B preparation which has not been reported in literature Methods and other issues, to achieve the effect of cheap and easy-to-obtain raw materials, consistent purity, and high yield

Inactive Publication Date: 2018-02-02
JIANGSU BAOZONG & BAODA PHARMACHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] European Pharmacopoeia version 8.0 mentions the chemical structure of the impurity 17-methylmorphinan-3-ol enantiomer (DXM-B) of DXM in Page 2025-2026, but there is no literature report on DXM-B Preparation

Method used

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  • Preparing method of dextromethorphan impurity 17-methylmorphinan-3-alcohol enantiomer (DXM-B)
  • Preparing method of dextromethorphan impurity 17-methylmorphinan-3-alcohol enantiomer (DXM-B)
  • Preparing method of dextromethorphan impurity 17-methylmorphinan-3-alcohol enantiomer (DXM-B)

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Embodiment 11

[0017] Example 1 Synthesis of 17-methylmorphinan-3-ol enantiomer (DXM-B)

[0018]

[0019] Put dextromethorphan hydrobromide monohydrate (20g, 54.05mmol), 48% hydrobromic acid (50g, 296.3mmol) and water (20g) into the reaction flask, heat up to reflux, and react for 24 hours. Cool down to room temperature, add water (100g), toluene (50g) and stir at room temperature. Adjust the pH to 8-9 with caustic soda (about 10 g), and stir for 15 minutes. The layers were allowed to stand, and the water layer was discarded. Water (100g) and caustic soda (4g, 100mmol) were added to the toluene layer and stirred for 15 minutes, the layers were left to stand, and the toluene layer was discarded. The aqueous layer was acidified with hydrochloric acid to pH 7-8, and a white solid was precipitated. Filtration, filter cake was added in 50% acetone water (50g), heated to dissolve, cooled to room temperature, precipitated white crystals, filtered, vacuum-dried to obtain 8.2 grams of product, ...

Embodiment 2

[0021] Put dextromethorphan base (20g, 73.8mmol), acetonitrile (120ml), boron trifluoride ether (25g, 176.1mmol) into the reaction bottle, under the protection of nitrogen, react at room temperature for 6 hours. The reaction solution was slowly added to water (200 g) and toluene (100 g), adjusted to pH 8-9 with liquid caustic soda, and stirred at room temperature for 15 minutes. The layers were allowed to stand, and the water layer was discarded. Water (100g) and caustic soda (6g, 150mmol) were added to the toluene layer and stirred for 15 minutes, the layers were left to stand, and the toluene layer was discarded. The aqueous layer was acidified with hydrochloric acid to pH 7-8, and a white solid was precipitated. Filtration, filter cake was added in 50% acetone water (80g), heated to dissolve, cooled to room temperature, precipitated white crystals, filtered, vacuum-dried to obtain 11 grams of product, yield 58%, purity 99.0% (HPLC, area normalized Chemical calculation)

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Abstract

The invention relates to a preparing method of a dextromethorphan impurity 17-methylmorphinan-3-alcohol enantiomer (DXM-B). Dextromethorphan serves as a raw material to be mixed and reacted with a demethylation reagent in a solvent, the reaction temperature is 20-150 DEG C, the reaction time is 1-72 h, through separation and purification, the 17-methylmorphinan-3-alcohol enantiomer is obtained, and the reaction equation of the 17-methylmorphinan-3-alcohol enantiomer is shown in the description. The preparing method of the 17-methylmorphinan-3-alcohol enantiomer has the advantages that the synthesis path is reasonable, the raw materials are cheap and easy to obtain, the operation is simple and feasible, the yield is high, and the purity meets requirements.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of dextromethorphan impurity 17-methylmorphinan-3-ol enantiomer. Background technique [0002] Dextromethorphan (DXM) is a powerful central antitussive drug, the antitussive strength is equivalent to codeine, long-term use or high doses will not produce drug resistance and addiction. It has been paid more and more attention and welcome in clinical application, and has become the most widely used antitussive drug with the largest quantity in the world. [0003] The chemical name of dextromethorphan is 3-methoxy-17-methylmorphinan enantiomer, whose structural formula is shown below [0004] [0005] During the synthesis process, dextromethorphan will be decomposed in an acidic environment to produce impurity DXM-B. Facing severe challenges in domestic and foreign markets, improving the quality of domestic dextromethorphan is an impor...

Claims

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Application Information

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IPC IPC(8): C07D221/28
CPCC07D221/28C07B2200/07
Inventor 姚胜宇唐明星徐小祥
Owner JIANGSU BAOZONG & BAODA PHARMACHEM
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