Novel method for preparing ramelteon key intermediate

A technology for ramelteon and intermediates, applied in the field of chemical and pharmaceutical industries, can solve the problems of low yield and achieve the effects of simple post-treatment, mild reaction conditions and high yield
CN102432571AInactive Publication Date: 2012-05-02CHINA PHARM UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
CHINA PHARM UNIV
Publication Date
2012-05-02
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention discloses a novel method for preparing a ramelteon key intermediate 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)ethylamine hydrochloride (I). The method is characterized by comprising the following steps of: performing dehydration condensation and heated decarboxylation on 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (II) and cyanoacetic acid (III) under the action of a catalyst to obtain a compound (IV); and directly hydrogenating and salifying the compound (IV) without separating and purifying to obtain the ramelteon key intermediate 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)ethylamine hydrochloride (I). The invention provides the novel method for preparing the ramelteon key intermediate hydrochloride (I). In the method, the cheap and readily available cyanoacetic acid (II) is used; and the method is high in yield and low in cost, is easy and convenient to operate, is environment-friendly and is suitable for industrialized production.
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Description

technical field

[0001] The invention belongs to the technical field of chemical industry and pharmacy, and relates to a new preparation method of ramelteon key intermediate hydrochloride. technical background

[0002] Ramelteon (ramelteon), chemical name (S)-N-[2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)]propane Amide, with the following structural formula, was developed by Japan's Takeda Company and was approved by the US FDA in September 2005. It is a new type of melatonin receptor agonist, which can selectively stimulate melatonin type 1 receptor and type 2 receptor (MT1, MT2), increase slow wave sleep (SWS) and rapid eye movement sleep (REW) , which helps to regulate the sleep cycle and improve sleep quality, is the first non-addictive insomnia drug that is not under special control.

[0003]

[0004] Ramelteon

[0005] 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)ethylamine hydrochloride is a key intermediate for the synthesis of ramelteon, its structura...

Claims

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