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Method for synthesizing 1-hydroxymethyl-2-aza adamantane and derivatives thereof

An azaadamantane and hydroxymethyl technology, which is applied in the field of synthesizing 1-hydroxymethyl-2-azaadamantane and derivatives thereof, can solve the problems of lengthy routes, harsh deprotection conditions, and no compounds are obtained, Achieve the effects of cheap raw materials and reagents, mild reaction conditions, and novel preparation methods

Active Publication Date: 2013-09-25
SHANGHAI AQ BIOPHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, this route is tedious, and Ts should be used as a protecting group on the nitrogen atom, and the deprotection conditions are harsh (under strong alkali conditions) or it is not easy to remove the protection.
In addition, the above reports only describe the preparation of 3-methyl-1-hydroxymethyl 2-azaadamantane
The substituted and unsubstituted synthesis at the 3-position requires a different route, and there is no substituted 1-hydroxymethyl-3-hydrogen-2-azadamantane at the 3-position mentioned in the present invention The preparation has not been reported yet
[0007] The present inventor once tried to prepare the compound shown in (III) from the direct alkali (KOH solution) hydrolysis of the compound shown in (I) in the following reaction formula, but the reaction product is very complicated, and the compound shown in (III) has never been obtained:

Method used

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  • Method for synthesizing 1-hydroxymethyl-2-aza adamantane and derivatives thereof
  • Method for synthesizing 1-hydroxymethyl-2-aza adamantane and derivatives thereof
  • Method for synthesizing 1-hydroxymethyl-2-aza adamantane and derivatives thereof

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Embodiment 1

[0023] 1.1 Synthesis of 3,4-(2'-azaadamantane)oxazolin-2-one

[0024]

[0025] The compound 1-iodomethyl-2-azadamantane hydrogen iodide salt (8g, prepared according to the document J.Am.Chem.Soc., 2006, 128, 26, 8412-8413) was dissolved in 100mL of methanol, Di-tert-butyl dicarbonate (9 g) was added, and 1N aqueous sodium carbonate solution was added dropwise with stirring to control pH=9-10. Stir at room temperature for 3 hours, TLC detected that the reaction was complete, spin off the methanol under reduced pressure, extract with ethyl acetate (50mL*3), combine the organic phases and dry with sodium sulfate, filter, and concentrate to dryness to give compound 3,4- (2'-Azaadamantane)oxazolin-2-one (8 g, not purified) was directly used in the next reaction.

[0026] 1.2 Synthesis of 1-hydroxymethyl-2-azaadamantane

[0027]

[0028] The compound 3,4-(2'-azaadamantane)oxazolin-2-one was dissolved in 50% potassium hydroxide solution (150 mL), and heated to reflux overnigh...

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Abstract

The invention provides a method for synthesizing 1-hydroxymethyl-3-hydrogen-2-aza adamantane. The method uses 1-iodomethyl-3-hydrogen -2-aza adamantane as raw materials to be reacted with di-tert-butyl dicarbonate ester, and an obtained intermediate opens rings in a strong basic solvent, to obtain 1-hydroxymethyl-3-hydrogen-2-aza adamantane shown in the formula (III). A reaction equation is shown in the specification. The preparation method has advantages of novelty, cheap raw materials and reagents, mild reaction condition and easy operation. The synthesized 1-hydroxymethyl-2-aza adamantane can be used as an important template or an intermediate for new medicine research and development.

Description

technical field [0001] The invention relates to a method for synthesizing 1-hydroxymethyl-2-azadamantane and its derivatives. Background technique [0002] Adamantane is a caged saturated hydrocarbon, its unique physical and chemical properties are determined by its rigid system and high symmetry structure. Adamantane and its derivatives are widely used in many fields such as medicine, pesticides, functional polymers, surfactants, and photosensitive materials. This kind of compound is mainly used for anti-influenza A virus in medicine. With the deepening of research, it is found that adamantane derivatives have various biological activities. For example, amantadine not only has the effect of anti-influenza virus, but also has anti-HSV virus and anti-fungal effects; another example is the dementia treatment drug memantine developed by the German Nerz company, which is used to treat moderate to severe dementia and has achieved good results , and has been marketed worldwide; ...

Claims

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Application Information

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IPC IPC(8): C07D471/08
Inventor 张会利单立人卢寿福
Owner SHANGHAI AQ BIOPHARMA CO LTD
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