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A method for synthesizing 1-hydroxymethyl-3-hydrogen-2-oxaadamantane and derivatives thereof

A technology for adamantane and hydroxymethyl, which is applied in the field of synthesizing 1-hydroxymethyl-3-hydro-2-oxadamantane and derivatives thereof, and can solve problems such as inability to synthesize

Active Publication Date: 2016-02-10
SHANGHAI AQ BIOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, the oxygen anion generated after the Grignard reaction continuously attacks the epoxy structure to obtain the product. The disadvantage of this method is that there must be a substituent (such as methyl, vinyl, etc.) on the 3-position.
Unable to synthesize 3-position unsubstituted 1-hydroxymethyl-3-hydrogen-2-oxaadamantane compound by the above method

Method used

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  • A method for synthesizing 1-hydroxymethyl-3-hydrogen-2-oxaadamantane and derivatives thereof
  • A method for synthesizing 1-hydroxymethyl-3-hydrogen-2-oxaadamantane and derivatives thereof
  • A method for synthesizing 1-hydroxymethyl-3-hydrogen-2-oxaadamantane and derivatives thereof

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Embodiment 1

[0021] 1.1 Synthesis of 7-methylenebicyclo-[3.3.1]-nonan-3-ol

[0022]

[0023] Compound 7-methylenebicyclo-[3.3.1]-nonan-3-one (14g, 93mmol) was dissolved in THF / MeOH (100mL / 20mL), cooled to below 10°C in an ice-water bath, and slowly divided into 5 Sodium borohydride (6 g, 158 mmol) was added in batches, and after the addition was complete, the reaction was warmed to room temperature and stirred for 5 hours. Spin to dry, dilute with ethyl acetate / water (200mL / 100mL), separate the organic phase and dry with anhydrous sodium sulfate, and spin dry to obtain 14g of crude product, which is directly used in the next reaction.

[0024] 1.2 Synthesis of 1-hydroxymethyl-2-oxaadamantane

[0025]

[0026] Compound 7-methylenebicyclo-[3.3.1]-nonan-3-ol was dissolved in dichloromethane (250mL), cooled to 0°C, and m-chloroperoxybenzoic acid (37.3g, 184 mmol), allowed to warm to room temperature after addition, and stirred overnight. TLC detected the completion of the reaction, co...

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Abstract

The invention relates to a method for synthesizing 1-hydroxymethyl-3-hydrogen-2-oxa adamantane and derivatives thereof, wherein the method comprises that: 7-methylene bicycle-[3.3.1]-nonane-3-ketone (I) as a raw material, is reduced by sodium borohydride, and an obtained intermediate (II) has no need to be purified, and is directly reacted with metachloroperbenzoic acid to obtain 1-hydroxymethyl-3-hydrogen-2-oxa adamantane and derivatives (III) thereof, wherein a reaction equation is show in the specification. The synthetic method has advantages of cheap raw materials and reagents, mild reaction condition and easy operation. The synthesized 1-hydroxymethyl-3-hydrogen-2-oxa adamantane (III) 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-3-hydrogen-2-oxaadamantane and its derivatives. Background technique [0002] Adamantane is a caged saturated hydrocarbon. Due to its rigid system and high symmetry structure, its unique physical and chemical properties are determined. 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. Alcohols in adamantane are important members of adamantane compounds, which are precursors for the synthesis of various highly active drugs such as adapalene and rimantadine, and are used for the prevention and treatment of type A influenza. [0003] The 1-hydroxymethyl-3-hydrogen-2-oxaadamantane involved in the prese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08
Inventor 张会利单人立卢寿福
Owner SHANGHAI AQ BIOPHARMA CO LTD