Preparation method of 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo (3.2.1)octane

A -4H-1, azabicycle technology, applied in organic chemistry and other directions, can solve the problems of low product yield and purity, interfere with recrystallization, etc., and achieve the effects of good product purity, complete reaction, and high yield
CN102766141AInactive Publication Date: 2012-11-07WENZHOU MEDICAL UNIV
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Patent Information

Authority / Receiving Office
CN Β· China
Patent Type
Applications(China)
Current Assignee / Owner
WENZHOU MEDICAL UNIV
Publication Date
2012-11-07
Estimated Expiration
Not applicable Β· inactive patent

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Abstract

The invention provides a preparation method of 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo(3.2.1)octane, which comprises the following steps successively: taking N-(8-benzyl-8-azabicyclo(3.2.1)oct-3-yl)-isobutyramide as a raw material and heating to reflux with a chlorinating agent in an aprotic solvent, then reacting with alcohol under the action of triethylamine to obtain isobutyl-N-(8-benzyl-8-azabicyclo(3.2.1)oct-3-yl)imidate, and heating to reflux with acetohydrazide in alcohol of C2-C5 to obtain 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo [3.2.1] octane crude, and finally purifying by n-heptane and ethyl acetate to obtain the target product with high purity. The 8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo [3.2.1] octane prepared by the method provided by the invention has the advantages of less byproducts, high yield and high product purity.
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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] 8-Benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane is a novel The key intermediate of the anti-AIDS drug Maraviroc (Maraviroc), the common point of the current synthesis route of this intermediate is that N-(8-benzyl-8-azabicyclo[3.2.1]octyl-3- Base) isobutyramide is chlorinated into N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)isobutyrimidic acid chloride, and then converted to N- (8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)isobutyric acid hydrazide, and then obtained 8-benzyl-3-(3-isopropyl- 5-Methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane (WO2008063600; WO2010040272; Organic Process Research & Development 2008,12,1094– 1103), the methods of different documents are only slightly different in the specific implementation of the route. ...

Claims

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