Novel synthesizing method of dapoxetine

A technology of dapoxetine and a synthesis method, applied in a new synthesis field, can solve the problems of complicated operation, unfavorable industrial production, high price and the like, and achieves the effects of cheap raw materials, low cost and simple separation

Inactive Publication Date: 2013-09-18
湖南欧亚药业有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

[0025] When this type of method is used for asymmetric catalytic hydrogenation, the chiral ligands and no

Method used

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  • Novel synthesizing method of dapoxetine
  • Novel synthesizing method of dapoxetine
  • Novel synthesizing method of dapoxetine

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Embodiment Construction

[0058] In order to make the technical means, creative features, work flow, and use methods of the present invention achieve the purpose and effect easily understood, the present invention will be further described below in conjunction with specific embodiments.

[0059]

[0060] I　

[0061]

[0062] II III

[0063]

[0064] III IV

[0065]

[0066] V

[0067]

[0068] VI VII

[0069] Synthesis of chiral catalyst (s)-α,α-diisopropyldimethyl-tert-butylsilyloxyprolinol:

[0070]

[0071] 1

[0072]

[0073] 2 3

[0074] Synthesis of Intermediate 1:

[0075] Add 31.2 grams of magnesium powder (1.30mol) and 50 milliliters of methyl tert-butyl ether into the reaction flask, under stirring, under nitrogen protection, slowly add 147.6 grams of 2-bromopropane (1.20mol) in methyl tert-butyl ether 500ml of ether solution (15ml will be added dropwise first, and after the reaction is triggered, slowly add the remaining solution...

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Abstract

The invention discloses a novel synthesizing method of dapoxetine, wherein a series of reactions are carried out on trans-cinnamaldehyde and N-carbobenzoxy hydroxylamine which serve as initiative raw materials under the action of a self-prepared catalyst (s)-alpha-alpha-diisopropyl dimethyl tert-butyl silicon oxygroup prolinol, so that an important intermediate of the dapoxetine, namely an important chiral intermediate (S)-3-amino-3-phenyl propyl alcohol (compound 4), is obtained. The invention further discloses a preparation method of capecitabine, wherein the compound serving as a raw material is methylated and protected by hydroxyl and then reacts with 1-naphthol to form a salt, so that the capecitabine is obtained. The preparation method is easy in raw material obtainment, good in stereoselectivity and high in yield, thereby being suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a new synthesis method of dapoxetine. Background technique [0002] Dapoxetine, compound 1, its chemical name is (S)-(+)-(N,N-dimethylamino)-3-(naphthyl-1-oxyl)amphetamine. Dapoxetine is a selective serotonin reuptake inhibitor, and its hydrochloride is used clinically. Early use in the treatment of depression and related affective disorders has not gained unanimous approval. Later research found its new use for the treatment of premature ejaculation symptoms in men. Launched in Finland and Sweden in February 2009, the drug has a short half-life, few adverse reactions, and remarkable effects. It is the first oral prescription drug approved in the world for the treatment of male premature ejaculation disorder. According to expert analysis, its annual sales can reach 500 million US dollars. [0003] [0004] At present, there are mainly two types of m...

Claims

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Application Information

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IPC IPC(8): C07C217/48C07C213/06C07C213/08B01J31/02C07F7/18
Inventor 林开朝
Owner 湖南欧亚药业有限公司
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