Synthesis method of 4,7-diazaspiro[2.5]octane compound

By adopting substitution, protecting group and esterification steps in the synthesis of 4,7-diazaspiro[2.5]octane compounds, the carbon-oxygen double bond reduction reaction is avoided, and the flammable and explosive problems in the existing technology are solved. and corrosive reagents, a safe and efficient synthesis of 7-benzyl-4,7-diazaspiro[2.5]octane was achieved.

CN111943893AActive Publication Date: 2020-11-17ADVENCHEN LAB NANJING +1
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2019-05-17
Publication Date
2020-11-17

AI Technical Summary

Technical Problem

In the existing synthesis method of 4,7-diazaspiro[2.5]octane compounds, boron trifluoride ether adduct and sodium borohydride are used to reduce the carbon-oxygen double bond, which is flammable, explosive and Corrosive toxicity issues limit industrial large-scale production.

Method used

Using derivatives of 4-methoxybenzyl (1-(hydroxymethyl)cyclopropyl) carbamate as raw materials, through the steps of substitution, adding protecting groups, esterification and deprotecting groups, carbon and oxygen are avoided. The reduction reaction of the double bond directly synthesizes 7-benzyl-4,7-diazaspiro[2.5]octane.

Benefits of technology

The safe and effective synthesis of 7-benzyl-4,7-diazaspiro[2.5]octane is achieved, avoiding the use of flammable, explosive and corrosive reagents, and improving production safety and efficiency.

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Abstract

The invention discloses a synthesis method of a 4,7-diazaspiro[2.5]octane compound, which comprises the following steps: by using a derivative of 4-methoxybenzyl-(1-(hydroxymethyl)cyclopropyl) carbamate as a raw material, substituting, adding a protecting group, esterifying, re-substituting, and removing the protecting group to obtain the 4,7-diazaspiro[2.5]octane compound. According to the synthetic route, the 4,7-diazaspiro[2.5]octane compound (such as 7-benzyl-4,7-diazaspiro[2.5]octane in the scheme) is directly obtained through the last step of cyclization, so that the problem of carbon-oxygen double bond reduction in the existing literature is avoided.
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