A kind of preparation method of pharmaceutical intermediate optically pure cyclopentenol

A technology of pure cyclopentenol and intermediates, applied in the direction of organic chemical methods, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of expensive reagents and high requirements for reaction conditions, and achieve low price, simple operation, and high reaction efficiency. The effect of mild conditions
CN107188786BActive Publication Date: 2021-10-22HUBEI GRAND LIFE SCI & TECH CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
HUBEI GRAND LIFE SCI & TECH CO LTD
Publication Date
2021-10-22

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Abstract

The present invention relates to a kind of preparation method of optically pure cyclopentenol of pharmaceutical intermediate, and this method is to use 3-butenal and its 3-position or 4-position derivative as raw material, in catalytic amount (S)-proline Synthesized in the presence of optically pure aldol condensation products, the aldehyde group was reduced to a hydroxyl group and then protected with benzyl bromide, and then obtained through a high-efficiency double bond metathesis ring-closure reaction (1 S ,2 R )-2-benzyloxymethylcyclopent-3-en-1-alcohol, the method provided by the invention has mild reaction conditions, cheap raw materials and reagents, high yield, and is suitable for industrial production.
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Description

technical field

[0001] The invention relates to the technical field of organic chemical industry, in particular to a method for preparing a pharmaceutical intermediate optically pure cyclopentenol. Background technique

[0002] (1S,2R)-2-Benzyloxymethylcyclopent-3-en-1-ol is an important pharmaceutical intermediate for the synthesis of carbocyclic nucleosides (Abdallah Ezzitouni, Pamela Russ, and Victor E. Marquez. J. Org. Chem. 1997, 62, 4870-4873), such as entecavir (GS Bisacchi et al, Bioorg Med Chem Lett, 1997, 7(2), 127-132).

[0003] Regarding the synthesis of (1S,2R)-2-benzyloxymethylcyclopent-3-en-1-ol, mainly using sodium cyclopentadiene as a raw material, the synthetic route is as follows:

[0004]

[0005] Sodium cyclopentadiene reacts with benzyl chloride methyl ether to obtain 5-benzyloxymethyl cyclopentadiene, and then carries out hydroboration reaction with dipinyl borane, and after oxidation, the target product (1S,2R)-2- Benzyloxymethylcyclopent-3-en-1-...

Claims

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