Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method for salmeterol

A technology of palladium carbon and compounds, applied in the field of preparation of salmeterol, can solve the problems of low yield and difficulty in applying industrial production, etc., and achieve the effects of high yield, low cost, and simple operation process and post-treatment

Inactive Publication Date: 2015-05-27
SHANGHAI INST OF PHARMA IND CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects that the existing method for preparing salmeterol by reductive ammoniation method needs to be purified by column chromatography, the yield is low, and it is difficult to be applied to industrial production, etc., and a kind of The preparation method of salmeterol

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
  • Preparation method for salmeterol
  • Preparation method for salmeterol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 0.4g (2.2mmol) of compound 1 and 0.5g (2mmol) of compound 2 to the autoclave successively, 0.05g mass fraction is 10%Pd / C, 50ml absolute ethanol, seal, pass into 2.0Mpa hydrogen, room temperature Stir for 12h. Filter, concentrate the filtrate, wash with 50ml of ethyl acetate, filter, adjust the pH of the filtrate to 2-3 with 2mol / L hydrochloric acid, separate layers, extract the ethyl acetate layer with water, combine the water layers, and adjust with saturated sodium bicarbonate solution The pH of the aqueous layer was 8-9, extracted with ethyl acetate, combined the ethyl acetate layers, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain an oil, which was stirred by adding 10ml of methyl tert-butyl ether 0.67 g of white solid salmeterol was precipitated, with a yield of 80.7%. The structural identification data of the product are as follows:

[0028] m.p.75-76°C (75-77°C repor...

Embodiment 2

[0033] Add 0.46g (2.5mmol) of compound 1 and 0.5g (2mmol) of compound 2 to the autoclave successively, 0.1g of mass fraction is 20%Pd / C, 50ml of absolute ethanol, seal it, pass into 2.0Mpa hydrogen, room temperature Stir for 24h. Filter, concentrate the filtrate, wash with 50ml of ethyl acetate, filter, adjust the pH of the filtrate to 2-3 with 2mol / L hydrochloric acid, separate layers, extract the ethyl acetate layer with water, combine the water layers, and adjust with saturated sodium bicarbonate solution The pH of the aqueous layer was 8-9, extracted with ethyl acetate, combined the ethyl acetate layers, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain an oil, which was stirred by adding 10ml of methyl tert-butyl ether , 0.68 g of salmeterol was precipitated as a white solid, with a yield of 81.9%. The structural identification data of the product are as follows:

[0034] m.p.76-77°...

Embodiment 3

[0039] Add 0.4g (2.2mmol) of compound 1 and 0.82g (3.3mmol) of compound 2 successively in the autoclave, the mass fraction of 0.04g is 10% Pd / C, 50ml of absolute ethanol, seal, and feed 2.0Mpa hydrogen, Stir at room temperature for 12h. Filter, concentrate the filtrate, wash with 50ml of ethyl acetate, filter, adjust the pH of the filtrate to 2-3 with 2mol / L hydrochloric acid, separate layers, extract the ethyl acetate layer with water, combine the water layers, and adjust with saturated sodium bicarbonate solution The pH of the aqueous layer was 8-9, extracted with ethyl acetate, combined the ethyl acetate layers, washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to obtain an oil, which was stirred by adding 10ml of methyl tert-butyl ether , 0.67 g of salmeterol was precipitated as a white solid, with a yield of 73.3%. The structural identification data of the product are as follows:

[0040] m.p...

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 discloses a preparation method for salmeterol expressed by formula 3. The preparation method comprises the following steps: in a solvent, under the catalysis of palladium carbon, causing the compound 1, compound 2 and hydrogen to be subjected to reduction ammoniation reaction, thereby obtaining the salmeterol. The preparation method provided by the invention has the advantages of mild reaction conditions, simple post-processing, lower cost, higher yield and easiness in realization of industrialization.

Description

technical field [0001] The present invention specifically relates to a preparation method of salmeterol. Background technique [0002] Preparation of salmeterol (GB1200886) mainly reports the following method with the method for reductive ammoniation: [0003] Add 0.5g (2.73mmol) of compound 1 and 0.5g (2mmol) of compound 2 to 5ml of methanol at 23°C, react for 0.5h, add 0.5g (13.2mmol) of sodium borohydride and continue stirring for 7h, add water to the reaction solution Extraction with ethyl acetate and column chromatography gave 0.25 g of the final product salmeterol with a yield of 30.1%. However, this method is difficult to be applied to industrial scale-up production due to problems such as column chromatography purification method and low yield. Contents of the invention [0004] The technical problem to be solved by the present invention is to overcome the defects that the existing method for preparing salmeterol by reductive ammoniation method needs to be puri...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/10C07C213/02
Inventor 肖旭华褚晓孙文劼袁博
Owner SHANGHAI INST OF PHARMA IND CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com