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Preparation method of octahydrocyclopentane[C]pyrrole

A technology of octahydrocyclopentane and pyrrole, which is applied in the field of preparation of octahydrocyclopentane[C]pyrrole, the key synthetic intermediate of drugs, and can solve the problems of the industrial production method of octahydrocyclopentane[C]pyrrole that has not been reported. , to achieve the effect of high product yield, high product yield and mild reaction

Inactive Publication Date: 2014-02-26
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] So far, no industrial production method of octahydrocyclopentane[C]pyrrole has been reported, and it is urgent to find a safe and high-yield effective industrial quantitative production method

Method used

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  • Preparation method of octahydrocyclopentane[C]pyrrole
  • Preparation method of octahydrocyclopentane[C]pyrrole

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Embodiment 1

[0029]

[0030] Under nitrogen atmosphere, tetrahydrofuran (500mL), toluene (1.5L), sodium borohydride (68.40g, 2.5eq.) and zinc chloride (125.0g, 1.3eq.). The resulting suspension was heated to reflux. The tetrahydrofuran was distilled off slowly, and the temperature was controlled at 90±5°C until a black solid was formed. A solution of cyclopentanimide (100 g, 0.72 mol) in tetrahydrofuran (500 mL) was added dropwise and refluxed at this temperature overnight. Cool, neutralize with dilute hydrochloric acid to pH=2-3, separate the organic phase, extract the aqueous phase with ethyl acetate (1L x3) three times, and separate the organic phase. The acidic aqueous layer was neutralized to pH=8-9 with saturated sodium carbonate solution, and then extracted with ethyl acetate (1L x3). The combined organic phases were dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Octahydrocyclopentane[C]pyrrole (72.8 g, 90.9%) was obtain...

Embodiment 2

[0032] Under nitrogen atmosphere, tetrahydrofuran (50mL), toluene (150mL), sodium borohydride (6.84g, 2.5eq.) and zinc chloride (12.5g, 1.3 eq.). The resulting suspension was heated to reflux. The tetrahydrofuran was distilled off slowly, and the temperature was controlled at 90±5°C until a black solid was formed. A solution of cyclopentanimide (10 g, 72 mmol) in tetrahydrofuran (50 mL) was added dropwise and refluxed at this temperature overnight. Cool, neutralize with dilute hydrochloric acid to pH=2-3, separate the organic phase, extract the aqueous phase with ethyl acetate (100mL x3) three times, and separate the organic phase. The acidic aqueous layer was neutralized to pH=8-9 with saturated sodium carbonate solution, and then extracted with ethyl acetate (100 mL x 3). The combined organic phases were dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Octahydrocyclopentane[C]pyrrole (7.35 g, 91.8%) was obtained as a ...

Embodiment 3

[0034]

[0035] Under nitrogen atmosphere, tetrahydrofuran (50mL), toluene (150mL), potassium borohydride (9.76g, 2.5eq.) and zinc chloride (14.4g, 1.5 eq.). The resulting suspension was heated to reflux. The tetrahydrofuran was distilled off slowly, and the temperature was controlled at 90±5°C until a black solid was formed. A solution of cyclopentanimide (10 g, 72 mmol) in tetrahydrofuran (50 mL) was added dropwise and refluxed at this temperature overnight. Cool, neutralize with dilute hydrochloric acid to pH=2-3, separate the organic phase, extract the aqueous phase with ethyl acetate (100mL x3) three times, and separate the organic phase. The acidic aqueous layer was neutralized to pH=8-9 with saturated sodium carbonate solution, and then extracted with ethyl acetate (100 mL x 3). The combined organic phases were dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Octahydrocyclopentane[C]pyrrole (7.33 g, 91.6%) was...

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Abstract

The invention provides a preparation method of octahydrocyclopentane[C]pyrrole. The preparation method is characterized in that under the promotion action of Lewis acid, by one step, a cyclopentylimide compound (II) is reduced into the octahydrocyclopentane[C]pyrrole (I) by a boron reducing agent.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a preparation method of octahydrocyclopenta[c]pyrrole (octahydrocyclopenta[c]pyrrole, CAS No. 5661-03-0), a key synthetic intermediate of medicine. Background technique [0002] Hepatitis C virus is a single-stranded linear positive-sense RNA virus. Because it can cause various chronic liver diseases, HCV is one of the main killers of human deaths due to diseases so far. In 2011, the U.S. Food and Drug Administration (FDA) approved two small-molecule drugs, Telaprevir and Boceprevir, to be marketed in the United States. The launch of these two protease inhibitors has changed the treatment effect of hepatitis C in the past ten years; this is a relatively big breakthrough in the field of hepatitis C treatment. [0003] Octahydrocyclopentane[C]pyrrole (or its salt) is a very useful pharmaceutical intermediate in drug synthesis. It is not only a key intermediate for the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/52
CPCC07D209/52
Inventor 赵长阔李晓飞王先恒王兴华
Owner ZUNYI MEDICAL UNIVERSITY
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