Chapter 5. Comparison of Four Technical Syntheses of Ethyl (R)-2-Hydroxy-4-Phenylbutyrate

  1. Dr. Hans-Ulrich Blaser3,
  2. Dr. Elke Schmidt4
  1. Dr. Hans-Ulrich Blaser3,
  2. Marco Eissen1,
  3. Pierre F. Fauquex2,
  4. Konrad Hungerbühler1,
  5. Dr. Elke Schmidt4,
  6. Gottfried Sedelmeier2,
  7. Martin Studer3

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch5

Book Title

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Additional Information

How to Cite

Blaser, H.-U., Eissen, M., Fauquex, P. F., Hungerbühler, K., Schmidt, E., Sedelmeier, G. and Studer, M. (2004) Comparison of Four Technical Syntheses of Ethyl (R)-2-Hydroxy-4-Phenylbutyrate, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (eds H.-U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602151.ch5

Editor Information

  1. 3

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  2. 4

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. 1

    Laboratory of Chemical Engineering, Swiss Federal Institute of Technology, Zürich, CH-8093 Zürich, Switzerland

  2. 2

    Novartis Pharma AG, Klybeckstrasse 141, CH-4057 Basel, Switzerland

  3. 3

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  4. 4

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Publication History

  1. Published Online: 13 JAN 2004
  2. Published Print: 6 NOV 2003

ISBN Information

Print ISBN: 9783527306312

Online ISBN: 9783527602155

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Keywords:

  • synthesis;
  • ethyl (R)-2-hydroxy-4-phenylbutyrate;
  • HPB ester;
  • enantioselective reduction;
  • keto acid 3;
  • Proteus vulgaris;
  • D-LDH;
  • enantioselective hydrogenation;
  • keto ester 5;
  • diketo ester 6

Summary

This chapter contains sections titled:

  • Introduction

  • Synthetic Pathways to HPB Ester

    • Route A: Synthesis and Enantioselective Reduction of Keto Acid 3 with Immobilized Proteus vulgaris Followed by Esterification

    • Route B: Enantioselective Reduction of 3 with D-LDH in a Membrane Reactor

    • Route C. Synthesis and Enantioselective Hydrogenation of Keto Ester 5

    • Route D: Synthesis and Enantioselective Hydrogenation of Diketo Ester 6, Followed by Hydrogenolysis

  • Comparison of Routes A–D with Respect to Mass Consumption, Environmental, Health and Safety Aspects

    • Definitions

    • Overall Material Masses Consumed and Produced for Routes A–D

    • Mass Consumption of the Reduction Systems A–D

    • Problematic Chemicals: Environmental, Health and Safety Aspects (EHS)

      • Safety Aspects

      • Health/Toxicology

      • Environment

  • Overall Comparison of Routes A–D and General Conclusions

    • Conclusions for the Reduction Steps

    • Conclusions for the Overall Syntheses

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