Continuous-Flow Synthesis of GABA derivatives

  • Author: ChemistryViews
  • Published: 20 April 2015
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Nature/Nature Publishing Group
thumbnail image: Continuous-Flow Synthesis of GABA derivatives

Continous-flow synthesis has several advantages over batch synthesis when it comes to reproducibility, automation, using higher pressures and temperatures, and safety. However, the synthesis of complex organic molecules, especially in the pharmaceutical industry, has been a challenge.

Shū Kobayashi and co-workers, University of Tokyo, Japan, have used a continuous-flow setup to synthesize both enantiomers of rolipram (pictured), a GABA (γ-aminobutyric acid) derivative and anti-inflammatory drug. The team used columns containing both achiral and chiral heterogeneous catalysts, and was able to produce the drug with high enantioselectivity in an eight-step process. Starting from a commercially available aldehyde and nitromethane, they obtained product on the gram scale. Other GABA derivatives could also be synthesized by slightly modifying the system and reactants.

The researchers found their system to be stable for at least a week, and showed that no metal from the employed catalysts found its way into the product. There was no need for isolation of intermediates or for the separation of catalysts, by-products, or excess reagents. The team is working on scaling up their system towards synthesis on a multi-kilogram scale.


Article Views: 3853

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH