Method for preparing 4-amino-adamantanecarboxylic acid

A technology of adamantanecarboxylic acid and amino group is applied in the preparation of organic compounds, chemical instruments and methods, cyanide reaction preparation and other directions, which can solve the problems of complex preparation method and high cost, and achieve cost reduction, good economic benefits, and operability. strong effect

Inactive Publication Date: 2015-09-23
上海博康精细化工有限公司
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of preparation method of 4-amino-adamantanecarboxylic acid, the prep

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing 4-amino-adamantanecarboxylic acid
  • Method for preparing 4-amino-adamantanecarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In a 2L reaction flask, add 100g of 4-carbonyl-adamantanecarboxylic acid and 500g of 7N NH 3 / MeOH solution, stirred at room temperature for 16 hours, cooled the reaction solution to 0°C, added 20g of sodium borohydride, stirred at 0-20°C for 4 hours, spin-dried the reaction solution, added 2L of water and stirred for 30 minutes, adjusted the pH to 5 with hydrochloric acid -6, continue to stir for 30 minutes, extract the reaction solution with 300mL dichloromethane for 3 times, combine the dichloromethane, spin dry, add 1L acetonitrile and 1L water to the solid, stir at room temperature for 10 hours, and obtain the solid product after suction filtration and drying. 90 g of product.

[0018] The NMR data are as follows:

[0019] 1H NMR (400MHz, CD3OD-d4) δ 3.36 (m, 1H), 2.03-1.53 ​​(m, 13H).

[0020] The material ratio is as follows:

[0021]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a method for preparing 4-amino-adamantanecarboxylic acid. 4-carbonyl-adamantanecarboxylic acid, five to ten N of NH<3>/MeOH solutions and sodium borohydride are firstly weighed, the 4-carbonyl-adamantanecarboxylic acid and the NH<3>/MeOH solutions are added into a reaction vessel and stirred at room temperature, reaction liquid is cooled to -5 DEG C to 2 DEG C, the sodium borohydride is added, stirring is carried out for two to six hours, the reaction liquid is spin-dried, water is added for dissolution, stirring is carried out, PH is adjusted to five to six through hydrochloric acid, stirring continues, the reaction liquid is extracted two to five times through first organic solvents, and the first organic solvents are combined. After spin-drying, second organic solvents and water are added into solids for dissolution, stirring is carried out for four to ten hours at room temperature, suction filtration is carried out, and the 4-amino-adamantanecarboxylic acid is obtained after solid products are dried. No high-pressure vessel is adopted, reactions are carried out in a common vessel, no noble metal catalyst is adopted, cost is lowered, no hydrogen gas reduction is adopted, high operability is achieved, and the industrial application prospect is achieved.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a pharmaceutical intermediate, specifically a preparation method of 4-amino-adamantanecarboxylic acid. Background technique [0002] 4-Amino-adamantanecarboxylic acid is a pharmaceutical intermediate used to prepare aminoadamantanecarboxylate derivatives, and the aminoadamantanecarboxylate derivatives can be used as raw materials or intermediate compounds for drug synthesis. 4-Amino-adamantanecarboxylic acid can be used to synthesize hypoglycemic drugs, weight loss drugs, anti-inflammatory agents, anti-ischemic drugs, anti-ischemic drugs, anti-asthma drugs, cholesterol-lowering drugs, anti-glaucoma drugs, and anti-hypertensive drugs. 4-Amino-adamantanecarboxylic acid can be applied to the synthesis of 11β-hydroxysteroid dehydrogenase type 1 enzyme inhibitor (11β-HSD-1). [0003] The currently published patents for the preparation of 4-amino-adamantanecarboxylic acid are as follo...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C229/50C07C227/08
Inventor 傅志伟贺宝元潘新刚牟立娟余文卿
Owner 上海博康精细化工有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap