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Method for synthesizing 3-azabicyclo[3,1,0]hexyl-1-aldehyde

A technology of azabicyclo and hexyl, which is applied in the fields of chemical pharmacy and fine chemical preparation, which can solve the problems of difficult preparation of substrates and narrow substrate range, and achieve the effects of difficult preparation, simple operation and novel structure

Active Publication Date: 2014-12-03
山东雪地铝业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] These methods have certain limitations, such as complex substrates that are difficult to prepare, and narrow substrate ranges.

Method used

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  • Method for synthesizing 3-azabicyclo[3,1,0]hexyl-1-aldehyde
  • Method for synthesizing 3-azabicyclo[3,1,0]hexyl-1-aldehyde
  • Method for synthesizing 3-azabicyclo[3,1,0]hexyl-1-aldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Mix 2 mmol of 1-p-toluenesulfonyltriazole 5a and 0.01 mmol of rhodium acetate in 10 ml of toluene and stir at a temperature of 120 degrees. After 2 hours, stop heating, add 2 ml of methanol, 5 mmol of potassium carbonate and 0.2 ml of water, stirred at room temperature for 8 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehyde 6a was obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 2

[0031] Mix 2 mmoles of 1-p-toluenesulfonyltriazole 5b and 0.1 mmoles of rhodium acetate in 10 ml of dichloroethane and stir at a temperature of 50 degrees. After 5 hours, stop heating, add 2 ml of methanol, 5 ml Molar potassium carbonate and a drop of water were stirred at room temperature for 12 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehyde 6b was obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

Embodiment 3

[0033] Control 120 degrees, after 10 minutes, stop heating, add 2 milliliters of methanol, 5 millimoles of potassium carbonate and a drop of water, stir at room temperature for 12 hours. Extract three times with the organic solvent ethyl acetate, combine the organic phases and wash with saturated brine, then dry with anhydrous sodium sulfate, evaporate the solvent under reduced pressure, use ethyl acetate and petroleum ether as eluents for the residue, and perform silica gel column chromatography After separation and purification, the corresponding nitrogen heterocyclic aldehyde 6c was obtained (see Table 1). Alternatively, after the reaction is completed, the organic solvent is evaporated under reduced pressure, and the residue is directly separated on a silica gel column.

[0034] Table 1. Preparation of 3-azabicyclo[3,1,0]hexyl-1-carbaldehyde

[0035]

[0036]

[0037]

[0038] 6a: 68%; 1 H NMR (400MHz, CDCl 3 )δ8.94(s,1H),7.98(d,J=8.4Hz,1H),7.71(p,J=7.2Hz,2H),7...

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Abstract

The invention discloses a method for synthesizing 3-azabicyclo[3,1,0]hexyl-1-aldehyde, belonging to the technical field of chemical pharmaceuticals and fine chemical preparation. The high-efficiency synthesis of polysubstitution 3-azabicyclo[3,1,0]hexyl-1-aldehyde can be realized, a metal-catalyzed sulfonyl triazole is used for decomposing into metal carbine, then the metal carbine is subjected to efficient cyclopropanation to obtain heterocyclic nitrogen with a unique structure, namely 3-azabicyclo[3,1,0]hexyl-1-formaldehyde. The method provides a new technological route for efficiently preparing functionalized N-allyl-3-indolal and 3-azabicyclo-[3,1,0]hexane derivatives, thus having wide application in the fields of chemical pharmaceuticals and fine chemicals.

Description

technical field [0001] The present invention relates to the preparation of nitrogen heterocyclic rings, that is, the efficient preparation route of 3-azabicyclo[3,1,0]hexyl-1-carbaldehyde, especially the metal-catalyzed carbene cyclization reaction, which efficiently generates multi-substituted functional groups nitrogen heterocycle. The present invention provides a new technical route and design strategy for efficiently preparing functionalized nitrogen-heterocyclic derivatives 3-azabicyclo[3,1,0]hexyl-1-carbaldehyde, which is useful in the fields of chemical pharmacy and fine chemical industry Wide applications belong to the technical fields of chemical pharmacy and fine chemical preparation. Background technique [0002] Nitrogen heterocycles are a large class of important organic compounds. Many nitrogen heterocycles have special chemical and biological activities, exist in many natural products and drug molecules, and are also used in functional materials. The nitroge...

Claims

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Application Information

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IPC IPC(8): C07D209/52
CPCC07D209/52
Inventor 徐华栋周浩徐科贾志宏沈美华
Owner 山东雪地铝业科技有限公司
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