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Method for synthesis of 1,8-diazaspiro [4,5] decane-3-hydroxy-1-benzyl-8-carboxylic acid tert-butyl ester

A technology of tert-butyl carboxylate and diazaspiro, applied in the field of organic synthesis

Active Publication Date: 2015-12-16
SHANGHAI TBBMED CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Bicyclic compounds have always been a difficult point in organic synthesis, and there are relatively few published documents and patents. The bicyclic compound 1,8-diazaspiro[4.5]decane-3-hydroxyl-1-benzyl-8-carboxylic acid The synthesis of tert-butyl ester (CAS: 1357353-34-4) has not been reported in the literature, and there are only three suppliers in the market

Method used

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  • Method for synthesis of 1,8-diazaspiro [4,5] decane-3-hydroxy-1-benzyl-8-carboxylic acid tert-butyl ester
  • Method for synthesis of 1,8-diazaspiro [4,5] decane-3-hydroxy-1-benzyl-8-carboxylic acid tert-butyl ester

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Experimental program
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Embodiment 1

[0017] The first step, in the reaction flask, add N-Boc-4-piperidone (8.0 g, 0.04 mol) and benzylamine (4.7 g, 0.044 mol) and 80 ml of toluene in sequence, then add 15 g of 4A molecular sieves, and heat up After the reaction was completed, the molecular sieve was filtered off, and the filtrate was rotary evaporated to dryness to obtain 11.9 g of the crude product of benzyl imine of formula II, which was directly used in the next reaction;

[0018] In the second step, under temperature control -10°C-0°C, dissolve 11.9 grams of benzyl imine of formula II in 77 ml of anhydrous tetrahydrofuran, and slowly add 1.4 equivalents of 2M allylmagnesium chloride tetrahydrofuran solution dropwise. After the reaction, The reaction was quenched by adding saturated ammonium chloride to pH=4. After the layers were separated, the organic layer was washed with saturated brine, and the organic layer was spin-dried to obtain 9.8 g of the crude product of the addition product formula III, which was ...

Embodiment 2

[0022] The first step, in the reaction flask, add N-Boc-4-piperidone (8.0 grams, 0.04 moles) and benzylamine (5.1 grams, 0.048 moles) and 80 milliliters of toluene successively, then add 15 grams of 4A molecular sieves, heat up After the reaction was completed, the molecular sieves were filtered off, the filtrate was rotary evaporated to dryness, and after column chromatography (n-hexane / ethyl acetate=15:1-10:1), 9.2 grams of benzyl imine of formula II were obtained, which were directly For the next step reaction;

[0023] The second step, under temperature control -10°C-0°C, dissolve 9.2 grams of benzyl imine of formula II in 100 ml of anhydrous tetrahydrofuran, slowly add 1.2 equivalents of 1M allylmagnesium bromide tetrahydrofuran solution dropwise, and the reaction ends Finally, add saturated ammonium chloride to quench the reaction until PH = 4-5, after layering, the organic layer was washed with saturated brine, and the organic layer was spin-dried to obtain 9.8 g of the...

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Abstract

The invention discloses a method for synthesis of the bicyclic compound 1,8-diazaspiro [4,5] decane-3-hydroxy-1-benzyl-8-carboxylic acid tert-butyl ester. The raw material N-Boc-4-piperidone easy to obtain is adopted, and the 1,8-diazaspiro [4,5] decane-3-hydroxy-1-benzyl-8-carboxylic acid tert-butyl ester is obtained through dehydration condensation reaction, allyl Grignard addition reaction, epoxidation reaction and proton abstraction ring-closing reaction which are conducted continuously.

Description

technical field [0001] The invention relates to a method for synthesizing bicyclic compound 1,8-diazaspiro[4.5]decane-3-hydroxyl-1-benzyl-8-carboxylic acid tert-butyl ester, which belongs to the field of organic synthesis. Background technique [0002] The azaspirobicyclic compounds can be used to synthesize orexin receptor antagonists for the prevention of nervous and mental disorders and to synthesize antimuscarinic active compounds. [0003] Bicyclic compounds have always been a difficult point in organic synthesis, and there are relatively few published documents and patents. The bicyclic compound 1,8-diazaspiro[4.5]decane-3-hydroxyl-1-benzyl-8-carboxylic acid The synthesis of tert-butyl ester (CAS: 1357353-34-4) has not been reported in the literature, and there are only three suppliers in the market. In order to better develop the application of this compound, it is urgent to find a relatively simple route to synthesize this compound. Contents of the invention [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/10
CPCC07D471/10
Inventor 高峰曾赛兰
Owner SHANGHAI TBBMED CO LTD
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