Preparation method for 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazole-4-base)-8-azabicyclo[3.2.1]octane

A technology of -4H-1 and azabicyclo, applied in the direction of organic chemistry, can solve the problems of interference recrystallization, low product yield and purity, etc., and achieve the effect of good product purity, simple operation and high yield
CN102584814AInactive Publication Date: 2012-07-18ZHEJIANG UNIV +1
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Patent Information

Authority / Receiving Office
CN ยท China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG UNIV
Publication Date
2012-07-18
Estimated Expiration
Not applicable ยท inactive patent

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Abstract

The invention discloses a preparation method for 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazole-4-base)-8-azabicyclo[3.2.1]octane. The preparation method comprises the following steps of: heating and refluxing N-(8-benzyl-8-azabicyclo[3.2.1]octyl-3-base)isobutyramide serving as a raw material and a vulcanization reagent in a non-proton solvent to obtain N-(8-benzyl-8-aza-bicyclo[3.2.1]octyl-3-base)isobutyl sulfamide; making sodium alcoholate react with halogenated hydrocarbon or sulfate to obtain N-(8-benzyl-8-aza-bicyclo[3.2.1]octyl-3-base)isobutyl imine acid thioester; heating and refluxing an alcohol with 2-5 carbon atoms and acethydrazide to obtain crude 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazole-4-base)-8-aza-bicyclo[3.2.1]octane; and refining normal heptane and ethyl acetate to obtain a high-purify target product. Due to the adoption of the method for preparing the 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazole-4-base)-8-azabicyclo[3.2.1]octane, water is prevented from interfering an intermediate reaction process, the yield is high, and the product purity is high.
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Description

technical field

[0001] The invention relates to the key intermediate 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazole-4- The preparation method of -8-azabicyclo [3.2.1] octane. Background technique

[0002] Maraviroc was approved by the US FDA and the European Commission in August and September 2007, respectively, for the treatment of patients with CCR5-tropic HIV-1 infection in combination with other antiretroviral drugs. A CCR5 antagonist and first oral entry inhibitor with significant first-to-market advantage. 8-Benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is a new anti- The key intermediate of the AIDS drug Maraviroc, the current route to synthesize this intermediate has in common that N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl ) isobutyramide is converted into N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl) isobutyric acid chloride by chlorination, and then converted into N-( 8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)isobutyrimidic acid hydraz...

Claims

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