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Amines in Pharmaceutical Synthesis

Amines in Pharmaceutical Synthesis
Contributors
Professor of Chemistry | University of Michigan, Flint
Associate Professor | Colorado College
Portfolio Manager for Education ACSGCI | American Chemical Society Green Chemistry Institute (ACS GCI)
Associate Professor | Radford University
Learning Objets
Summary
This module explores the synthesis of amines with a focus on the reductive amination reaction. Numerous examples from the discovery and commercial manufacturing of pharmaceuticals are included. After an introduction to traditional reductive amination methods, students evaluate the traditional methods using green chemistry principles and systems thinking approaches. Students also compare traditional methods to newer technologies, including greener chemical methods and bioenzymatic reduction processes. Students are introduced to key concepts in systems thinking and explore connections between multistep synthesis of amine-containing pharmaceuticals and UN SDGs 3 (Good Health and Well-Being) and 12 (Responsible Production and Consumption). To scaffold student learning on systems thinking topics, Unit 1 focuses primarily on laboratory scale synthesis and systems within the laboratory, with attention to laboratory worker safety. Unit 2 broadens systems thinking topics to include larger scale syntheses, including manufacturing processes, and systems beyond the laboratory, such as environmental systems.

Module Goal: Students will be able to explain the mechanism for the reductive amination process and apply this reaction toward proposed syntheses of amines in pharmaceuticals. Using green chemistry principles and systems thinking analysis, students will identify benefits and limitations of reductive amination methods by comparing traditional methods, alternative green reagents, and enzymatic processes. Finally, students will critique the multistep discovery and manufacturing processes for amine-containing pharmaceuticals using green chemistry principles, systems thinking analysis, and connection to the UN Sustainability Goals (e.g., Goals 3 and 12).


The GCTLC learning object external link takes you to the ACS GCI website to download the learning materials. Once there, use the Module Overview document to guide you through using these impactful learning materials.

This module was developed by Amy Dounay and Jessica Tischler for the green chemistry educational module project with the American Chemical Society Green Chemistry Institute; Sarah Kennedy and David Laviska reviewed and published the module.
Learning Goals/Student Objectives
LO A: Categorize amines as 1°, 2°, 3°

LO B: Draw detailed mechanisms for reductive amination reactions

LO C: Predict products for traditional reductive aminations

LO D: Apply the reductive amination reaction in synthesis of amines by proposing appropriate starting materials and reagents to complete a targeted synthesis.

LO E: Use Safety Data Sheets (SDSs) to identify key hazards of reagents and to consider how reaction scale (e.g., g vs. kg) impacts laboratory worker safety, risk assessment, and management planning

LO F: Provide examples of ways in which green chemistry and systems thinking can be used to improve processes for synthesis of pharmaceuticals.

LO G: Using systems thinking terminology, evaluate a chemical reaction in a reaction flask as a system and define its inputs and outputs.

LO H: Describe connections between green chemistry, systems thinking, and students’ individual/personal learning and future career goals.

LO I: Articulate specific ways in which chemists can directly impact UN SDGs through key decisions in the design, synthesis, and production of pharmaceuticals

LO J: Use principles of green chemistry and systems thinking to identify strengths and weaknesses of classical, updated, and biocatalytic reductive amination protocols.

LO K: Use green chemistry and systems-thinking approaches to recommend the best method for a chemical synthesis.

LO L: Explain how the purpose and scale of drug synthesis affects choices and impacts (e.g., discovery research scale vs. manufacturing scale).

LO M: Use systems thinking and SOCMEs to illustrate how a pharmaceutical product participates in multiple interacting systems.


Object Type
Lecture or course slides/notes (e.g., PPT, Prezi, PDF)
Lesson summaries
Exam questions and answers
Case studies
Small resource sets
Audience
Introductory Undergraduate
Upper/Advanced Undergraduate
Other Faculty Educators/Teachers
Common pedagogies covered
Collaborative/cooperative learning
Problem-based learning
Green Chemistry Principles
Waste Prevention
Less Hazardous Chemical Syntheses
Designing Safer Chemicals
Safer Solvents and Auxiliaries
Catalysis
U.N. Sustainable Development Goals (SDGs)
Good Health and Well-Being
Responsible Consumption and Production
Safety Precautions, Hazards, and Risk Assessment
N/A
Teacher Recommendations or Piloting Data (if available)
The module overview document in the link contains details about piloting this module in two learning environments.

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