Preparation method of (s)-3-hydroxytetrahydrofuran and (r)-3-hydroxytetrahydrofuran

Abstract

The invention discloses a preparation method of (S)-3-hydroxytetrahydrofuran and (R)-3-hydroxytetrahydrofuran, relating to the technical field of preparation of five-element heterocyclic compounds containing one oxygen atom as the only heterocyclic atom. The method comprises the following steps: by using (S)-carnitine or (R)-carnitine as the initial raw material, carrying out reduction reaction in a reducer and an organic solvent to obtain (S) or (R)-2,4-dihydroxy-N,N,N-trimethyl butyl amine alkali; adding a hydrogen chloride organic solvent solution into an organic solvent to perform salification reaction to obtain (S) or (R)-2,4-dihydroxy-N,N,N-trimethyl butyl amine hydrochloride; and finally, adding alkali into a polar solvent, heating, and carrying out cyclization reaction to obtain the (S) or (R)-3-hydroxytetrahydrofuran. The method has the advantages of low cost, simple technique, high yield, cheap and accessible raw materials, short reaction steps, short period and low pollution, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to the technical field of preparation of five-membered heterocyclic compounds containing one oxygen atom as the only heterocyclic atom. Background technique [0002] Regarding the synthesis of (S)-3-hydroxytetrahydrofuran, there are some related reports in China recently. The current chemical synthesis method mostly uses (S)-4-chloro-3-hydroxybutyric acid ethyl ester as the raw material, after reduction Then, the target product is synthesized by removing the hydrogen chloride ring under acidic conditions. Although the synthesis steps of this method are short, the required raw materials are expensive and the cost is high, and it is difficult to realize industrialization. [0003] Chemical. Research and Application.Vol.21, No.7.July.2009 reported that L-malic acid was used as the starting material, and (S)-dimethyl malate was produced by methylation with thionyl chloride / methanol. , and then reduce it with sodium borohydrid...

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Problems solved by technology

[0002] Regarding the synthesis of (S)-3-hydroxytetrahydrofuran, there have been some relevant reports in China recently. Most of the current chemical synthesis methods use (S)-4-chloro-3-hydroxybutyric acid ethyl ester as raw material. Finally, the target product is synthesized by removing the hydrogen chloride ring under acidic conditions. Although the synthesis steps of this method are short, the required raw materials are expensive and the cost is high, so it is difficult to realize industrialization.

[0003] Chemical. Research and Application.Vol.21, No.7.July.2009 reported that L-malic acid was used as the starting material to produce (S)-dimethyl malate through methyl esterification with thionyl chloride / methanol , and then reduced with sodium borohydride / sodium carbonate to generate 1,2,4-butanetriol, and then dehydrated and ring-closed with p-toluenesulfonic acid to generate (S)-3-hydroxytetrahydrofuran. The starting materials of this method are cheap and easy to obtain. The reaction steps are short, but p-toluenesulfonic acid is used in the last step, which makes the product difficult to purify and the yield is not high

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