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Preparation method of 1-methyl-3-pyrrolidinol

A technology of pyrrolidinol and methyl, which is applied in the field of preparation of 1-methyl-3-pyrrolidinol, can solve the problems of low yield and difficulty in large-scale production, so as to improve the purity, improve product quality and reduce the difficulty of purification Effect

Pending Publication Date: 2021-08-31
ZHEJIANG QIMING BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In order to improve 1-methyl-3-pyrrolidinol in the preparation process of the low yield, difficult to expand production problems, the application provides a preparation method of 1-methyl-3-pyrrolidinol

Method used

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  • Preparation method of 1-methyl-3-pyrrolidinol
  • Preparation method of 1-methyl-3-pyrrolidinol
  • Preparation method of 1-methyl-3-pyrrolidinol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A preparation method of 1-methyl-3-pyrrolidinol, comprising the steps of:

[0053] S1. Compound I and Compound II are subjected to a ring-closing reaction to obtain Compound III;

[0054] S2, reducing the compound III obtained in step S1 and the reducing agent IV to obtain 1-methyl-3-pyrrolidinol;

[0055] Among them, compound I is Compound II is H 3 CNH 2 , compound III is

[0056] Step S1 specifically includes the following sub-steps:

[0057] S1-1. Take 420.0g of toluene (solvent A) and add it to a 1L reaction flask, take 60.0g of malic acid (compound I), and 41.6g of 40% aqueous solution of methylamine (compound II) and drop them into a 1L reaction flask, Control the temperature in the 1L reaction bottle to stir at 15°C, control the stirring time to 0.5h, heat to reflux in the 1L reaction bottle, and divide the water for 18 hours;

[0058]S1-2. Sampling and testing. After the reaction is over, cool down and concentrate to remove toluene (solvent A), add 6g ...

Embodiment 2

[0065] A preparation method of 1-methyl-3-pyrrolidinol, comprising the steps of:

[0066] S1. Compound I and Compound II are subjected to a ring-closing reaction to obtain Compound III;

[0067] S2, reducing the compound III obtained in step S1 and the reducing agent IV to obtain 1-methyl-3-pyrrolidinol;

[0068] Among them, compound I is Compound II is H 3 CNH 2 , compound III is

[0069] Step S1 specifically includes the following sub-steps:

[0070] S1-1. Take 420.0g of xylene (solvent A) and add it to a 1L reaction flask, take 60.0g of malic acid (compound I), and 43.2g of 40% aqueous solution of methylamine (compound II) and add them dropwise to a 1L reaction flask In the process, the temperature in the 1L reaction bottle was controlled to be stirred at 15°C, the stirring time was controlled to be 0.5h, heated to reflux in the 1L reaction bottle, and the water was separated for 14 hours;

[0071] S1-2. Sampling and testing. After the reaction is over, cool down a...

Embodiment 3

[0078] A preparation method of 1-methyl-3-pyrrolidinol, comprising the steps of:

[0079] S1. Compound I and Compound II are subjected to a ring-closing reaction to obtain Compound III;

[0080] S2, reducing the compound III obtained in step S1 and the reducing agent IV to obtain 1-methyl-3-pyrrolidinol;

[0081] Among them, compound I is Compound II is H 3 CNH 2 , compound III is

[0082] Step S1 specifically includes the following sub-steps:

[0083] S1-1. Take 420.0g of chlorobenzene (solvent A) and add it to a 1L reaction flask, take 60.0g of malic acid (compound I), and 43.2g of 40% aqueous solution of methylamine (compound II) and drop them into a 1L reaction flask , control the temperature in the 1L reaction bottle to stir under the condition of 15°C, control the stirring time to 0.5h, heat to reflux in the 1L reaction bottle, and divide the water for 10 hours;

[0084] S1-2. Sampling and testing. After the reaction is finished, reduce the temperature and conce...

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Abstract

The invention relates to the technical field of synthesis of medical intermediates, and particularly discloses a preparation method of 1-methyl-3-pyrrolidinol. The preparation method comprises the following steps that S1, a compound I and a compound II are subjected to a ring closing reaction, so a compound III is obtained; and S2, the compound III obtained in the step S1 and a reducing agent IV are subjected to a reduction reaction, so 1-methyl-3-pyrrolidinol is obtained, wherein the compound I, the compound II and the compound III are as shown in the specification; and the reducing agent IV is one or more selected from a group consisting of sodium borohydride, potassium borohydride, boron trifluoride-diethyl ether and boron tribromide-diethyl ether. According to the preparation method, the compound II and the compound I are selected and subjected to the ring closing reaction to obtain the intermediate compound III, and the compound III is solid and is easy to crystallize and purify, so the purification difficulty of the intermediate is reduced, the purity of the intermediate is favorably improved, and the product quality of the 1-methyl-3-pyrrolidinol is further improved.

Description

technical field [0001] The application relates to the technical field of synthesis of pharmaceutical intermediates, more specifically, it relates to a preparation method of 1-methyl-3-pyrrolidinol. Background technique [0002] 1-Methyl-3-pyrrolidinol, also known as N-methyl-3-pyrrolidinol, 3-hydroxy-1-methylpyrrolidine, N-methyl-3-hydroxytetrahydropyrrole, 1-methyl Base-3-hydroxy-tetrahydropyrrole and N-methyl-3-hydroxypyrrolidinol are key intermediates for the synthesis of new anticholinergic drugs. [0003] In the related art, the preparation method of 1-methyl-3-pyrrolidinol mainly contains the following kinds: [0004] JMC, 2008, 15, 4609 reported that using glycine methyl ester as the starting material, condensing with ethyl chloroformate and then closing the ring with ethyl acrylate, proceeding with five-step reactions including hydrolysis decarboxylation, carbonyl reduction, and methylation reaction. target product. [0005] [0006] This method has the disadva...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/12C07D207/416
CPCC07D207/12C07D207/416
Inventor 姜旭琦鲁承勇薛入源
Owner ZHEJIANG QIMING BIOCHEM TECH
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