Preparation method of Ramelteon intermediate

A technology for ramelteon and intermediates, which is applied in the field of preparation of ramelteon intermediates, can solve the problems of unsuitability for large-scale industrial production, difficult control of reaction conditions, complicated reaction steps, etc., and achieve mature reaction mechanism and conditions Gentle, easy-to-step results

Active Publication Date: 2014-02-12
BEIJING WINSUNNY PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process of preparing intermediate (7) in this reaction route is easy to produce by-products, and the separation and purification of by-products obtained by Knoevenagel condensation reaction from intermediate (7) is difficult, the reaction conditions are not easy to control, and the yield is low.
And this reaction route reaction step is complicated, and operation is loaded down with trivial details, is not suitable for industrialized large-scale production

Method used

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  • Preparation method of Ramelteon intermediate
  • Preparation method of Ramelteon intermediate
  • Preparation method of Ramelteon intermediate

Examples

Experimental program
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Effect test

Embodiment Construction

[0043] Example 1 (method 1)

[0044] At a temperature of 0-5°C, dissolve 3.4g of 60% NaH and 22.5g of 2-(diethoxyphosphono)acetic acid in 300mL of toluene, rise to room temperature and stir to dissolve, add 19.0g of compound I, Raise the temperature to 90-100°C and stir. The high performance liquid chromatography detects that the reaction is complete. The reaction liquid is cooled and added to water, stirred, the organic phase is separated, and dried to obtain 19.2 g of compound II with a yield of 89.7%.

[0045] 1.8 g of 10% Pd / C and 18.5 g of compound II were dissolved in 200 mL of ethanol, and hydrogen gas was introduced. TLC showed that the reaction was complete. After filtration, the filtrate was concentrated to obtain 9.58 g of intermediate III, with a yield of 88.9%.

[0046] Example 2 (method 1)

[0047]At a temperature of 0-5°C, dissolve 8.9g of potassium tert-butoxide and 21g of quaternary phosphonium triphenylacetate in 280mL of dimethyl sulfoxide, rise to room ...

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Abstract

The invention relates to a preparation method of a Ramelteon intermediate. The Ramelteon intermediate is prepared by taking 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one as a raw material, and then subjecting the raw material to a series of simple reactions so as to obtain the Ramelteon intermediate. The preparation method of the Ramelteon intermediate has the advantages of high yield, high product purity, simple operation, low cost, and suitability for mass production.

Description

field of invention [0001] The present invention relates to the preparation method of ramelteon intermediate, specifically for the preparation of 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetic acid method. Background technique [0002] Ramelteon, the chemical name is (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propane Amide, the structural formula is: [0003] [0004] Ramelteon, developed by Takeda Corporation of Japan, is a potent and highly selective melatonin receptor agonist that acts on the melatonin hormone MT in the suprachiasmatic nucleus (also known as the circadian clock). 1 and MT 2 receptor. Ramelteon on MT 1 Receptor affinity, selectivity and potency are greater than melatonin, while MT 1 Receptors are in turn thought to be an integral part of the body's sleep regulation. Unlike benzodiazepines, ramelteon does not reduce rapid eye movement (REM) sleep in humans and is the first prescription treatment for insomnia without abus...

Claims

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Application Information

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IPC IPC(8): C07D307/77
CPCC07D307/77
Inventor 林国良张晓斌黄瑶耿玉先产运霞黄玉锋
Owner BEIJING WINSUNNY PHARMA CO LTD
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