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Method for preparing (s)-3-hydroxytetrahydrofuran

A technology of hydroxytetrahydrofuran and silicon tetrachloride, applied in organic chemistry methods, organic chemistry and other directions, can solve problems such as hidden safety hazards, low optical purity, and difficulty in product extraction, and achieve less by-products, high optical purity, and easy product separation. Effect

Inactive Publication Date: 2018-05-18
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis route of the first method is relatively mild, its product extraction is difficult and the optical purity is low; although the raw material cost of the second method is low, it needs to use flammable and explosive lithium aluminum hydride in the preparation process, which has potential safety hazards. At the same time, there is still the problem of low optical purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A preparation method for (s)-3-hydroxytetrahydrofuran, comprising the following steps:

[0021] (1) After mixing L-malic acid and methanol evenly, add silicon tetrachloride, heat to 40°C, reflux for 2 hours, then add sodium carbonate to adjust the pH to 7, after the reaction is completed, filter, extract, concentrate under reduced pressure, After drying, L-dimethyl malate was obtained;

[0022] (2) Dissolve the prepared L-dimethyl malate in absolute ethanol, add SbCl 3 and zinc powder, stir and mix evenly, heat to 50°C, reflux for 1 hour, then filter, add water, filter, and distill under reduced pressure to obtain the crude product of (s)-1,2,4-butanetriol;

[0023] (3) Mix the prepared (s)-1,2,4-butanetriol crude product with DMC (dimethyl carbonate), after mixing evenly, raise the temperature to 60°C, add Na 2 CO 3 The solution was stirred and reacted for 3 hours, and then fractionated under reduced pressure to obtain the (s)-3-hydroxytetrahydrofuran.

[0024] In ...

Embodiment 2

[0029] A preparation method for (s)-3-hydroxytetrahydrofuran, comprising the following steps:

[0030] (1) After mixing L-malic acid and methanol evenly, add silicon tetrachloride, heat to 50°C, reflux for 3 hours, then add sodium carbonate to adjust the pH to 9, after the reaction is completed, filter, extract, concentrate under reduced pressure, After drying, L-dimethyl malate was obtained;

[0031] (2) Dissolve the prepared L-dimethyl malate in absolute ethanol, add SbCl 3 and zinc powder, stir and mix evenly, heat to 60°C, reflux for 2 hours, then filter, add water, filter, and distill under reduced pressure to obtain the crude product of (s)-1,2,4-butanetriol;

[0032] (3) Mix the prepared (s)-1,2,4-butanetriol crude product with DMC (dimethyl carbonate), after mixing evenly, raise the temperature to 70°C, add Na 2 CO 3 The solution was stirred and reacted for 4 hours, and then fractionated under reduced pressure to obtain the (s)-3-hydroxytetrahydrofuran.

[0033] In...

Embodiment 3

[0038] A preparation method for (s)-3-hydroxytetrahydrofuran, comprising the following steps:

[0039](1) After mixing L-malic acid and methanol evenly, add silicon tetrachloride, heat to 40°C, reflux for 3 hours, then add sodium carbonate to adjust the pH to 7, after the reaction is completed, filter, extract, concentrate under reduced pressure, After drying, L-dimethyl malate was obtained;

[0040] (2) Dissolve the prepared L-dimethyl malate in absolute ethanol, add SbCl 3 and zinc powder, stir and mix evenly, heat to 60°C, reflux for 1 hour, then filter, add water, filter, and distill under reduced pressure to obtain the crude product of (s)-1,2,4-butanetriol;

[0041] (3) Mix the prepared (s)-1,2,4-butanetriol crude product with DMC (dimethyl carbonate), after mixing evenly, raise the temperature to 70°C, add Na 2 CO 3 The solution was stirred and reacted for 3 hours, and then fractionated under reduced pressure to obtain the (s)-3-hydroxytetrahydrofuran.

[0042] In s...

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PUM

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Abstract

The invention discloses a method for preparing (s)-3-hydroxytetrahydrofuran. The method comprises the following steps: mixing a prepared crude (s)-1,2,4-butanetriol with DMC (dimethyl carbonate); after uniform mixing, carrying out heating to 60-70 DEG C, adding a Na<2>CO<3> solution and carrying out a reaction for 3-4 h under stirring; and then carrying out pressure-reduced distillation to prepare(s)-3-hydroxytetrahydrofuran. The preparation method of the invention is low in requirements on operating conditions, high in safety, few in byproducts during the reaction, and high in product purityand yield.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of (s)-3-hydroxytetrahydrofuran. Background technique [0002] N-oxygen heterocyclic structures are widely found in various natural products and drugs, and the more common aliphatic heterocyclic rings containing nitrogen and oxygen include tetrahydrofuran, tetrahydropyran, morpholine, tetrahydropyrrole, piperidine and piperazine, etc. Among them, tetrahydrofuran and its derivatives are common structures in drugs. For example, the anticancer drug gemcitabine contains a multi-substituted chiral tetrahydrofuran. Gemcitabine is a difluoronucleoside antimetabolite anticancer drug that destroys cell replication. It is a water-soluble analog of deoxycytidine, which is an inhibitory enzyme substitute for ribonucleotide reductase; using tetrahydrofuran derivatives, it can also synthesize antiepileptic drug topiramate, antifungal drug posaconazole and antire...

Claims

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Application Information

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IPC IPC(8): C07D307/20
CPCC07B2200/07C07D307/20
Inventor 胡海威
Owner ITIC MEDCHEM CO LTD
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