A kind of process method of synthesizing 4-heteroatom substituted cyclohexenyl halides

A technology of cyclohexenyl group and process method, applied in the field of organic compound synthesis, can solve problems such as difficult control and harsh reaction conditions, and achieve the effects of simple operation, mild process conditions and simple synthesis route
CN102070586BActive Publication Date: 2016-04-27DALIAN NETCHEM CHIRAL TECH
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
DALIAN NETCHEM CHIRAL TECH
Publication Date
2016-04-27

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Abstract

The present invention relates to a method for synthesizing organic compounds. A process for synthesizing 4-heteroatom substituted cyclohexenyl halides, from cyclohexanone substituted by 4-heteroatom ( 1 ) starting with 1-50 equivalents of anhydrous hydrazine or hydrazine hydrate in a solvent, -20? oC to reflux reaction, after filtering or spin-drying the solvent to obtain the corresponding hydrazone, and then react with CuX2 / alkali mixture in alcohol solvent, the reaction temperature is -20? cC~40? oC, add alkaline aqueous solution and solvent after the reaction, obtain a mixed solution after liquid separation, add an organic base for reflux reaction, add 1N acid to remove the excess alkali, add saturated NaHSO3 for reaction, and remove the solvent to obtain a 4-position heteroatom Substituted cyclohexenyl halides ( 3 ). The synthesis process route of the present invention has originality, simple route, mild process conditions, simple and convenient operation, avoids the ultra-low temperature reaction and column chromatography purification involved in the literature, and is suitable for industrial scale-up production.
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Description

technical field

[0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing a 4-heteroatom substituted cyclohexenyl halide. Background technique

[0002] The cyclohexene structure with a heteroatom at the 4th position is often introduced into drug molecules as an important structural unit, or used for coupling reactions to obtain pharmaceutically active compounds. As the precursor of this type of structure, there are few reports on the synthesis of cyclohexenyl halides substituted by heteroatoms at the 4-position, and all of them inevitably require ultra-low temperature operation and column chromatography purification, which greatly limits their industrialization. aspects of application. existing literature [1] The synthetic route is as follows: starting from commercially available 4-position protected (such as NCbz, NBoc) cyclohexanone, using LiHMDS as base in THF solvent, -78 o After the reaction at C, maintain...

Claims

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