Synthesis process of levonorgestrel by methoxydienone

A technology of levonorgestrel and Worth's substance, which is applied in the technical field of synthesizing levonorgestrel from Worth's substance, can solve the problems of difficult reaction and the like, and achieves fast reaction speed, easy control of production conditions and process conditions. simple effect

Active Publication Date: 2012-09-26
NENTER & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a solution to the problem that the reaction is difficult to carry out due to the reaction of acetylene gas and potassium hydroxide to generate water in the existing production process

Method used

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  • Synthesis process of levonorgestrel by methoxydienone
  • Synthesis process of levonorgestrel by methoxydienone
  • Synthesis process of levonorgestrel by methoxydienone

Examples

Experimental program
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Effect test

Embodiment 1

[0028] The preparation of the first step alkynyl lithium ammonia complex:

[0029] a. Inject 500ml of liquid ammonia into a 1000ml three-necked reaction bottle, and control the temperature in the bottle at -55 to -50°C, add 10.5g of lithium metal under stirring, and add the time for 20 minutes;

[0030] b. After the lithium metal is completely dissolved in the liquid ammonia, control the temperature inside the bottle at -50°C, and feed acetylene gas into the bottle at a flow rate of 4L / min until the liquid ammonia solution changes from blue-black to gray-white, and then feed acetylene Gas 5min;

[0031] c. Use normal temperature water to heat up the outside of the reaction bottle, continue to volatilize liquid ammonia, and add 600ml methyl tert-butyl ether at the same time to make it react;

[0032] d. When the volume of the reaction liquid in the reaction bottle reaches 500ml after adding methyl tert-butyl ether, add a coolant to the reaction bottle to reduce the temperature...

Embodiment 2

[0041] The preparation of the first step alkynyl lithium ammonia complex:

[0042] a. Inject 500ml of liquid ammonia into a 1000ml three-necked reaction bottle, and control the temperature in the bottle at -55 to -50°C, add 11g of lithium metal under stirring, and add the time for 20 minutes;

[0043] b. After the lithium metal is completely dissolved in the liquid ammonia, control the temperature inside the bottle at -50°C, and feed acetylene gas into the bottle at a flow rate of 4L / min until the liquid ammonia solution changes from blue-black to gray-white, and then feed acetylene Gas 5min;

[0044] c. Heat up with normal temperature water on the outside of the reaction bottle, continue to volatilize liquid ammonia, and add 500ml toluene at the same time to make it react;

[0045] d. When the temperature of the reaction liquid in the reaction bottle reaches 10°C after adding toluene, add a coolant to the reaction bottle to reduce the temperature of the reaction liquid in th...

Embodiment 3

[0054] The preparation of the first step alkynyl lithium ammonia complex:

[0055] a. Inject 500ml of liquid ammonia into a 1000ml three-necked reaction bottle, and control the temperature in the bottle at -55 to -50°C, add 10.5g of lithium metal under stirring, and add the time for 20 minutes;

[0056] b. After the lithium metal is completely dissolved in the liquid ammonia, control the temperature inside the bottle at -50°C, and feed acetylene gas into the bottle at a flow rate of 4L / min until the liquid ammonia solution changes from blue-black to gray-white, and then feed acetylene Gas 5min;

[0057] c. Use normal temperature water to heat up the outside of the reaction bottle, continue to volatilize liquid ammonia, and add 600ml tetrahydrofuran to make it react;

[0058] d. When the volume of the reaction liquid in the reaction bottle reaches 500ml after adding tetrahydrofuran, add a coolant to the reaction bottle to reduce the temperature of the reaction liquid in the re...

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Abstract

The invention relates to a synthesis process of levonorgestrel, in particular to a synthesis process of levonorgestrel by methoxydienone. The synthesis process of the levonorgestrel uses the methoxydienone as a raw material which reacts with an alkynyllithium ammine complex to prepare an acetylide, and then the acetylide is hydrolyzed to obtain the levonorgestrel. The chemical structural formula in the process route is shown in the specification. The synthesis process has simple and easily controlled industrial production conditions, fast reaction speed, and low production cost. The synthesisprocess of the invention enhances the yield, further ensures the product quality, and solves the problems of the existing production processes that the solubility of the acetylene gas in the tetrahydrofuran is limited which results in the waste of the acetylene gas in a large amount, and the acetylene gas reacts with the potassium hydroxide to generate water, which has an influence on the reaction progress and can not meet the requirement of the industrial production of the levonorgestrel.

Description

Technical field: [0001] The invention relates to a process for synthesizing levonorgestrel, in particular to a process for synthesizing levonorgestrel from a Woshi compound. Background technique: [0002] Levonorgestrel is a known compound with the chemical name (-)-13-ethyl-17-hydroxy-18,19-didemethyl-17α-pregna-4-ene-20-yne-3 - Ketone, English name Levonorgestrel. Levonorgestrel is a quick-acting, short-term oral contraceptive. The contraceptive mechanism is to significantly inhibit ovulation and prevent implantation of fertile eggs, increase the thickness of cervical mucus, and increase the penetration resistance of sperm, thereby exerting a quick-acting contraceptive effect. The existing production process of levonorgestrel is as follows: pass acetylene gas into tetrahydrofuran dissolved with potassium hydroxide to saturation, lower the temperature to make saturated acetylene solution of tetrahydrofuran; use Woshi oxide as raw material, dissolve it in A solution prepar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J1/00
Inventor 蔡东伟吴喜英
Owner NENTER & CO
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