Preparation method of ent-(14S)-3-methoxyl-17-morphinan

A technology of methylmorphan and methoxy, which is applied in the field of preparation of ent--3-methoxy-17-methylmorphan, can solve the impurity ent-(14S)-3 which has not been specifically reported for dextromethorphan -Methoxy-17-methylmorphan preparation method, difficulties and other issues, to achieve the effect of high purity and simple process

Active Publication Date: 2015-03-25
山东立新制药有限公司
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Problems solved by technology

Thus trying to obtain ent-(14S)-3-methoxy-17-methylmorphan (D) by separation is very difficult
[0008] The current published literature does not specifically report the preparation method of dextromethorphan impurity ent-(14S)-3-methoxyl-17-methylmorphan (D)

Method used

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  • Preparation method of ent-(14S)-3-methoxyl-17-morphinan
  • Preparation method of ent-(14S)-3-methoxyl-17-morphinan
  • Preparation method of ent-(14S)-3-methoxyl-17-morphinan

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[0022] How to prepare ent-(14S)-3-methoxy-17-methylmorphan (D) simply and conveniently using the above-mentioned technical solution will be described below through a specific preparation process and method.

[0023] Add (+)-N-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-octahydro Isoquinoline (I) (2.7g, 10mmol), dichloromethane 25mL, start stirring, and add aluminum trichloride (3.3g, 25mmol) in batches. Slowly raise the temperature to 40°C, vigorously stir the reaction for 5 hours, TLC detection, the reaction is complete. The solid was removed by filtration, washed successively with sodium bicarbonate solution and water, the organic phases were combined, dried and concentrated under reduced pressure to obtain a pale yellow oil ent-(14S)-3-methoxy-17-methylmorphan (D) 2.4 g, yield 88.6%. The purity was 98.5% by high performance liquid chromatography (HPLC). The chromatographic conditions are: Waters symmetry C18 / 280 nm / 25°C / acetonitrile:water=60:40 (containing docusate sodium...

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Abstract

The invention discloses a preparation method of ent-(14S)-3-methoxyl-17-morphinan. The method comprises the following step of: enabling (+)-N-methyl-1-(4- methoxyl) benzyl-1,2,3,4,5,6,7,8-octahydro isoquinoline (I) to be subjected to cyclization reaction under the action of lewis acid, so as to produce the high-purity ent-(14S)-3-methoxyl-17-morphinan (D). The preparation method is simple in process, the prepared product is high in purity, and in comparison with the standard substance, the purity of the product is completely consistent with that of the standard substance.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis method design and preparation of raw materials and intermediates, and particularly relates to a preparation method of ent-(14S)-3-methoxy-17-methylmorphan. Background technique [0002] Dextromethorphan (ent-3-methoxy-17-methylmorphan) is the dextroisomer of morphine-like levomorphan methyl ether, which exerts a central antitussive effect by inhibiting the medullary cough center. It is a powerful central antitussive. Due to the low drug resistance and addiction of this variety, it is an antitussive drug suitable for long-term use or high-dose use. The drug has been included in the pharmacopoeia of many countries, and it is one of the important varieties that our country focuses on developing in this field. [0003] [0004] The pharmaceutical form of dextromethorphan is usually the ammonium salt of an acid, most commonly the hydrobromide salt. Since process and degradation impuriti...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/28
Inventor 许学农苏健王喆冷秀云
Owner 山东立新制药有限公司
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