Expert Details

Expert in Mechanistic Organic Chemistry

Expert ID: 723800 Missouri, USA

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Reaction mechanisms are at the core of his understanding of organic chemistry. Throughout his career, Expert's approach to chemical problems has been to perform careful experiments to determine the mechanism that is operating. Once that is determined, it becomes much easier to plan methods to improve the performance of the reaction. An example would be his patent on the dynamic resolution of a ketone. He used the enolization of an amino ketone to racemize it while preparing an acidic diastereomeric salt. The salt was at a pH of about 4 and caused the ketone to enolize. One of the optical isomers precipitated, while the material in solution kept reequilibrating. Ultimately 90% of the material precipitated as the wanted material. This is a good example of using mechanistic knowledge to produce the desired outcome.

His group of 3 people were challenged to develop a synthesis of physostigmine from scratch. After reviewing the methods out there he devised what he felt was a superior alternative. The group pursued the best literature method and his method in parallel. After 2 months of work, all work was moved to this innovative method as it had achieved more successes in that time than the literature method. In the two months they had completed 4 steps of the ultimate 9 step procedure. The method had come about due to computer modelling of a suggested starting material. Its indication of a predominant reactive site on a cheap indole derivative allowed a different starting material with a novel approach.

In his 30 years on the bench, he has run across many unique chemical separations. Some have been found by accident while others have been predicted. A particular one that he was pleased with was done by pKa. He had related two organic acids that clearly should have had at least 1-2 pKa units difference in acidity. He estimated the proportions by by NMR. With the mixture dissolved in a non-polar solvent, He added enough triethyl amine to be protonated by the stronger. It dropped out of solution leaving the weaker unprotonated acid in solution. Chemical separations often don't have rules. They must be dealt with on an individual basis taking the particular problem into account.

Much of his time has been spent working on natural products. The company he worked for made all of the opioid pain relievers and he has worked on many of them. He has synthesized and purified the cannabinoids and one of the purifications is in the process of being patented. He has a lot of experience in working with natural products and troubleshooting impurity removal.

He is experienced in structural identification of organic compounds. He has participated in x-ray crystallography identifications and prepared the pure samples of unknowns for identifications. he has experience in stereochemistry and have identified particular stereoisomers in a mixture.

He has worked in the organic laboratory for over 30 years. In that time, he has found that his expertise in organic chemistry allows him to be a first class troubleshooter of existing processes. Using his mechanistic approach, he can approach a problem and often eliminate it adjusting some of the parameters such as solvent and temperature based on the mechanism. He is also capable of molecular modeling and that and that can sometimes suggest the appropriate reaction controls.

He is familiar with a broad range of organic compounds and how to safely deal with them. This comes from over 30 years of working safely in the laboratory.

He learns organic reactions by their mechanisms. Reactions can be grouped by the mechanisms that they react by. This allows him to see the "forest through the trees" and use and change the reactions based on similarities with other reactions. Those similarities can guide him on how to improve the characteristics of the reaction currently being worked on.

It is the nature of organic chemistry to be qualitative. In most of the work he has done, he first confirms that the starting material is what it is supposed to be. He then reacts it, and identifies the products. The process of identifying the various functional groups that are changed or are not changed in a given process is an adventure in qualitative organic chemistry.

Expert may consult nationally and internationally, and is also local to the following cities: Saint Louis, Missouri - Columbia, Missouri - Saint Charles, Missouri - Saint Peters, Missouri - Florissant, Missouri - Springfield, Illinois

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Education

Year Degree Subject Institution
Year: 1976 Degree: Post-Doctoral Subject: Organic Chemistry Institution: University of Arizona
Year: 1975 Degree: Ph.D. Subject: Organic Chemistry Institution: Saint Louis University
Year: 1970 Degree: ACS approved B.S. in chemistry Subject: chemistry Institution: Saint Louis University

Work History

Years Employer Title Department Responsibilities
Years: 1984 to 2005 Employer: Mallinckrodt Chemical Company Title: Senior Research Associate Department: Research and Development Responsibilities: Conducted independent research on new products; did plant support at times on existing products; led small groups in research projects from time to time.
Years: 1981 to 1984 Employer: Sigma-Aldrich Chemical Company Title: Plant troubleshooter Department: Production IV Responsibilities: Troubleshooter for small, medium and large scale processes. Expert also was temporary plant manager when normal leader was sick or on vacation.
Years: 1980 to 1981 Employer: Ash-Stevens Chemical Company Title: Manager Department: Pilot Plant Responsibilities: Pilot Plant manager in charge of 7 chemists and a secretary. We made experimental drugs and compounds for the government along with a catalog of 150 compounds.
Years: 1976 to 1980 Employer: University of North Florida Title: Assistant Professor Department: Natural Sciences Dept. Responsibilities: Developed and taught 6 courses including Organic Chemistry I and II, Organic Mechanisms, Instrumental Analysis, Advanced Organic Synthesis.

Career Accomplishments

Associations / Societies
American Chemical Society;
Organic subsection;
Computer subsection;
Publications and Patents Summary
Expert has about 6 patents and 2 or 3 to still come out from his work. Expert has about 11 professional publications. Expert has written several observational books in astronomy.

Additional Experience

Expert Witness Experience
While teaching Expert did work for the public defender's office in Jacksonville, FL. This included some lab work. Expert did no trial work however because none of the things he worked on came to trial.
Training / Seminars
Three years ago Expert gave a seminar on using Molecular Modelling in organic synthesis to the research groups at Mallinckrodt.
Expert was liaison to a joint project we had with the University of Missouri. In conjunction with that work he developed a series of meetings called Synthesis Workshops where R&D folks would get together and brainstorm synthetic methods for new products.
Marketing Experience
Expert has coordinated efforts with our marketing people by doing molecular graphics for their presentations, visiting occasionally with clients and the FDA in Washington.
Other Relevant Experience
Expert was considered a "natural consultant", and an internal consultant for other chemists projects while at Mallinckrodt. They also used Expert for his last several years there as a mentor for younger chemists.

Language Skills

Language Proficiency
German He can read through German scientific articles and obtain experimental information accurately. He cannot read or write German.

Fields of Expertise

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