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Chiral synthesis of Eszopiclone

A technology of eszopiclone and chiral synthesis, which is applied in the field of medicine, and can solve the problems of long preparation route, low atom utilization rate of split technology, and high production cost

Inactive Publication Date: 2012-09-19
SHANGHAI ZNBIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The prior art has the following deficiencies: 1. Equal amounts of eszopiclone and zopiclone are obtained by splitting, wherein eszopiclone is useless, and the atomic utilization rate of the splitting technique is low; 2. The preparation route is long and the production cost high

Method used

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  • Chiral synthesis of Eszopiclone
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Examples

Experimental program
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Effect test

Embodiment 1

[0015] 6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine (compound 1, 23.4 g, 0.09 mol ) was added in 200 milliliters of tetrahydrofuran, then the solution of potassium borohydride (3.1 grams, 0.054mol) / D-proline (6.2 grams, 0.054mol) was added dropwise in 50 milliliters of tetrahydrofuran, and the reaction was stirred at room temperature for 5 hours. The liquid was slowly washed into 2 liters of water, and the solid was precipitated, left to stand, filtered with suction, washed with water, and dried to obtain 6-(5-chloro-2-pyridyl)-5(S)-hydroxyl-7-oxo-6 , 16.4 g of yellow powder of 7-dihydro-5H-pyrrolo(3,4-b)pyrazine (compound 2). (70% molar yield)

Embodiment 2

[0017] 6-(5-chloro-2-pyridyl)-5(S)-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine (compound 2, 4.5 gram, 0.018mol) was added in 50 milliliters of dichloromethane, added successively triethylamine (7 milliliters, 0.051mol), 1-chloroformyl-N-methylpiperazine hydrochloride (compound 3, 5.1 grams, 0.026 mol), reflux reaction for 3 hours, cooling, suction filtration, the mother liquor was concentrated to dryness, added 100 milliliters of water and stirred evenly, suction filtration, washing with water, drying, acetonitrile crystallization, obtained 4.0 grams of eszopiclone (compound 4) off-white crystalline powder . (molar yield 57%)

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Abstract

The invention relates to a chiral synthesis method for Eszopiclone and belongs to the technical field of medicine. The chiral synthesis method for Eszopiclone comprises the following two steps of reaction: (1), reducing under the action of a 6-(5-chlorine-2-pyridyl)-5,6-dioxo-6,7-dihydro-5H-pyrrol(3,4-b)pyrazine chiral reagent to obtain 6-(5-chlorine-2-pyridyl)-5(S)-hydroxyl-7-oxo-6,7-dihydro-5H-pyrrol(3,4-b)pyrazine; and (2), reacting the 6-(5-chlorine-2-pyridyl)-5(S)-hydroxyl-7-oxo-6,7- dihydro-5H-pyrrol(3,4-b)pyrazine with 1-chloroformyl-4-methylpiperazine hydrochloride under the action of organic base to obtain the Eszopiclone. The chiral synthesis method for the Eszopiclone has the advantages of high atom utilization ratio, short steps and advanced technology.

Description

technical field [0001] The invention relates to a preparation method in the technical field of medicine, in particular to a chiral synthesis method of eszopiclone. technical background [0002] Eszopiclone (Eszopiclone) is the latest generation of sedative-hypnotics developed by Sepracor Corporation of the United States, which was first launched in the United States in December 2004. This product is the first drug approved for long-term use in the treatment of insomnia. It can be used for long-term use to improve the onset of sleep (difficulty falling asleep) and maintain sleep quality (wake up at night or wake up too early in the morning), and has a broad market prospect. [0003] The document retrieval of prior art finds, prior art (such as Tetrahedron: Asymmetry 8,995-997,1997; Tetrahedron: Asymmetry11,4623-4627,2000) prepares eszopiclone generally first synthetic zopiclone, then use Chemical or biological resolution to obtain monochiral eszopiclone. The prior art has t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 武传宝
Owner SHANGHAI ZNBIOCHEM
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