Continuous Flow to Pure Amines

  • Author: Vikki Cantrill
  • Published: 18 March 2013
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Organic and Biomolecular Chemistry/RSC Publishing
thumbnail image: Continuous Flow to Pure Amines

Optically pure amines are key chiral auxiliaries and intermediates in the pharmaceutical and agrochemical industries. Many synthetic procedures for chiral amines are scope limited and use environmentally harmful reagents; however, chemoenzymatic dynamic resolution seems the most versatile.

Rodrigo O. M. A. de Souza and colleagues, Federal University of Rio de Janeiro, Brazil, have developed a method for the kinetic resolution of (+/-)-1-phenylethylamine (pictured) that uses continuous-flow conditions. Starting from the racemic amine, reaction with a supported enzyme – Candida Antarctica lipase B immobilized on Novozyme 435 – and ethyl acetate gives a pure chiral amide product with an enantiomeric ratio >200.

This low-cost procedure performs well with short reaction times (40 m), high conversion rates, mild temperatures (50 °C), and reusable catalyst (at least 9 times without loss of activity) that make it suitable for automation and scale-up.

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