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High Yielding Continuous-Flow Synthesis of Norketamine.

Marcos Veguillas Hernando1, Jonathan C Moore1, Rowena A Howie2

  • 1School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.

Organic Process Research & Development
|May 16, 2022
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Summary

A novel continuous-flow process synthesizes the antidepressant precursor norketamine. This safer, high-yielding method converts a batch process, reducing hazards from chemicals like liquid bromine and ammonia.

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Area of Science:

  • Chemical Engineering
  • Organic Synthesis
  • Pharmaceutical Chemistry

Background:

  • Norketamine is a key intermediate for antidepressant drug development.
  • Traditional batch synthesis of norketamine involves hazardous reagents and challenging scale-up.
  • Continuous-flow chemistry offers potential for safer and more efficient pharmaceutical manufacturing.

Purpose of the Study:

  • To develop a continuous-flow process for synthesizing norketamine.
  • To adapt a known batch synthesis route to a multi-stage flow platform.
  • To improve safety and efficiency in norketamine production.

Main Methods:

  • Telescoped multi-stage continuous-flow synthesis.
  • Incorporation of α-bromination of a ketone.
  • Utilizing imination/rearrangement with liquid ammonia.
  • Employing thermally induced α-iminol rearrangement.

Main Results:

  • Successful synthesis of pharmaceutical intermediate norketamine (5) via continuous flow.
  • High-yielding process with demonstrated scalability.
  • Significant reduction in hazards associated with liquid bromine, hydrogen bromide gas, and liquid ammonia handling.

Conclusions:

  • Continuous-flow synthesis offers a safer and more efficient alternative to batch processing for norketamine production.
  • The developed process mitigates key operational hazards inherent in traditional batch methods.
  • This approach supports the scalable and sustainable manufacturing of antidepressant precursors.