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

Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative

Active Publication Date: 2007-01-03
APELOA PHARM CO LTD +2
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Chinese patent CN1298867A takes (1R, 3S)-(+)-camphoric acid as a resolving agent, and equimolar (±)-alpha-methylaminopropiophenone and (1R, 3S)-(+)-camphoric acid are placed In ethanol, heat to dissolve, cool and crystallize, and separate (R)-(+)-α-methylaminopropiophenone (1R, 3S)-(+)-camphoric acid; The required (S)-(-)-α-methylaminopropiophenone (1R, 3S)-(+)-camphoric acid needs to undergo heating and cooling processes, and the preparation process is relatively complicated
Due to the instability of α-methylaminopropiophenone, after heating for 15-31h, a side reaction occurred, and the recovery rate of α-methylaminopropiophenone was low

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 of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative
  • Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Resolution method of (±)-α-methylaminopropiophenone 1

[0038] Dissolve 24.2g (±)-α-methylaminopropiophenone in 80ml methanol, slowly add dropwise a mixed solution consisting of 27.2g (2R, 3R)-(-)-dibenzoyltartaric acid and 80ml methanol, while stirring, After the dropwise addition, 400ml of ethyl acetate was slowly added and left for 16h, a large amount of solids were precipitated. Filter, wash with a little 2:5 mixed solvent of methanol and ethyl acetate, and dry to obtain 40.3g [(S)-(-)-α-methylaminopropiophenone] 2 ·(2R,3R)-(-)-dibenzoyl tartrate, mp140-142℃, [α] D -102.0° (c=1.0, CH 3 OH), the resolution optical yield was 158.7%.

[0039] The salt was placed in an aqueous solution of sodium carbonate, the temperature was controlled below 5°C, and extracted with dichloromethane. Distill out dichloromethane to obtain (S)-(-)-α-methylaminopropiophenone.

Embodiment 2

[0041] Resolution method of (±)-α-methylaminopropiophenone 2

[0042] Dissolve 24.2g (±)-α-methylaminopropiophenone in 400ml ethyl acetate, slowly add dropwise under stirring solution, a large amount of solids precipitated during the dropping process, and the solution was placed for 16 hours after the dropping. Filter, wash with a little 2:5 mixed solvent of methanol and ethyl acetate, and dry to obtain 37.0g [(S)-(-)-α-methylaminopropiophenone] 2 (2R,3R)-(-)-Dibenzoyl tartrate, mp140-142℃, [α] D -102° (c=1.0, CH 3 OH). Resolution optical yield 145.9%.

[0043] The salt was placed in an aqueous solution of sodium carbonate, the temperature was controlled below 5°C, and extracted with dichloromethane. Distill out dichloromethane to obtain (S)-(-)-α-methylaminopropiophenone.

Embodiment 3

[0045] Resolution method of (±)-α-methylaminopropiophenone 3

[0046] Dissolve 27.2g (2R, 3R)-(-)-dibenzoyl tartaric acid in 400ml ethyl acetate, slowly add dropwise under stirring solution, a large amount of solids precipitated during the dropwise addition, and continued to stir for 16 hours after the dropwise addition. Filter, wash with a little 2:5 mixed solvent of methanol and ethyl acetate, and dry to obtain 38.1g [(S)-(-)-α-methylaminopropiophenone] 2 ·(2R,3R)-(-)-dibenzoyl tartrate, mp140-142℃, [α] D -102° (c=1.0, CH 3 OH), the resolution optical yield was 150.2%.

[0047] The salt was placed in an aqueous solution of sodium carbonate, the temperature was controlled below 5°C, and extracted with dichloromethane. Distill out dichloromethane to obtain (S)-(-)-α-methylaminopropiophenone.

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

A process for preparing [(S)-(-)-alpha-methylaminophenyl acetone]2.(2R,3R)-tartarate derivative includes such steps as reaction between (+ / -)-alpha-methylaminophenyl acetone, (R)-(+)-alpha-methylaminophenyl acetone, or the (R)-(t)-(+)-alpha-methylaminophenyl acetone containing (S)-(-)-alpha-methylaminophenyl acetone and (2R, 3R)-tartarate derivative in solvent, and conventionally collecting target product.

Description

technical field [0001] The present invention relates to an intermediate for the preparation of (1R,2S)-(-)-ephedrine: [(S)-(-)-α-methylaminopropiophenone] 2 - Preparation method of (2R,3R)-tartaric acid derivatives. Background technique [0002] (S)-(-)-α-methylaminopropiophenone or (S)-(-)-α-methylaminopropiophenone salt is an important pharmaceutical intermediate, which can be used to prepare (1R, 2S)- (-)-Ephedrine. [0003] [(S)-(-)-α-Methylaminopropiophenone] 2 ·(2R,3R)-tartaric acid derivatives are generally prepared by resolving the compound (±)-α-methylaminopropiophenone. [0004] Chinese patent CN1298867A takes (1R, 3S)-(+)-camphoric acid as a resolving agent, and equimolar (±)-alpha-methylaminopropiophenone and (1R, 3S)-(+)-camphoric acid are placed In ethanol, heat to dissolve, cool and crystallize, and separate (R)-(+)-α-methylaminopropiophenone (1R, 3S)-(+)-camphoric acid; The required (S)-(-)-α-methylaminopropiophenone (1R, 3S)-(+)-camphoric acid needs to ...

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): C07C221/00C07C225/16
CPCC07B2200/07C07C221/00
Inventor 黄成军周后元
Owner APELOA PHARM 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