Synthesis method of 1,7-diazaspiro[3.5]nonane-7-tert-butyl formate

A synthetic method and a diazaspiro technology are applied in the field of chemical synthesis, can solve problems such as discomfort, and achieve the effects of cheap and easy-to-obtain raw materials, high yield, and simple post-processing operations.

Inactive Publication Date: 2021-08-06
SHANGHAI SYNTHEALL PHARM CO LTD
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Problems solved by technology

At present, although there are a small amount of literature reports (WO2017 / 216726, 2017, A1) on the synthetic method of 1,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester, because dangerous reagents and Odor reagent, not suitable for industrial scale-up production

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  • Synthesis method of 1,7-diazaspiro[3.5]nonane-7-tert-butyl formate
  • Synthesis method of 1,7-diazaspiro[3.5]nonane-7-tert-butyl formate
  • Synthesis method of 1,7-diazaspiro[3.5]nonane-7-tert-butyl formate

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[0046] The technical solution of the present invention will be clearly and completely described below, obviously, the described embodiments are part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

[0047] The reaction formula of the present invention is as follows:

[0048]

[0049] Step 1: Two batches of reactions run in parallel

[0050] Compound 1 (1 kg, 5.03 mol), compound 2 (884 g, 6.03 mol) and ammonium acetate (580.96 g, 7.545 mol) were added to ethanol (5 L), heated to 100° C., and refluxed for 16 hrs. TLC (petroleum ether / ethyl acetate=5 / 1) monitoring showed that the starting material was completely reacted. Combine two batches of reaction solutions in parallel reactions, concentrate under reduced pressure to obtain an oily c...

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Abstract

The invention provides a process synthesis method of 1,7-diazaspiro[3.5]nonane-7-tert-butyl formate. The synthesis method comprises the following five steps: 1, reacting a compound 1 with a bromine compound 2 and ammonium acetate by a one-pot method to obtain a compound 2; 2, reducing a compound 3 by using lithium borohydride to obtain a compound 4; 3, using triethylamine is used as alkali, and reacting the compound 4 with p-toluene sulfonyl chloride to generate a compound 5; 4, under the catalysis of potassium iodide, taking cesium carbonate as alkali, and carrying out ring closing on the compound 5 to generate a compound 6; and 5, under the action of magnesium chips, removing p-toluene sulfonyl from the compound 6 to obtain a compound 7. The method mainly solves the technical problem that no method suitable for industrial synthesis exists at present, and has the advantages that raw materials are easy to obtain, the total yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis methods, in particular to a method for synthesizing tert-butyl 1,7-diazaspiro[3.5]nonane-7-carboxylate. Background technique [0002] Compound 1,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester (CAS: 1180112-41-7) and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, although there are a small amount of literature reports (WO2017 / 216726, 2017, A1) on the synthetic method of 1,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester, because dangerous reagents and Odor reagent, not suitable for industrial scale-up production. [0003] Therefore, it is necessary to develop a synthetic method with cheap raw materials, convenient operation, relatively safe reaction, easy control, suitable overall yield and suitable for industrial production. Contents of the invention [0004] The technical problem to be solved by the present invention is to ...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10Y02P20/55
Inventor 周强张大为孙春于凌波徐学芹毛延军董径超马汝建徐艳白有银谭汝鹏王曦卫维贾涛冯瑞赵艳美
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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