Flow electrosynthesis: an enabling technology for sustainable synthesis of pharmaceuticals
Lead Research Organisation:
University of Southampton
Department Name: Sch of Chemistry
Abstract
The project seeks to exploit novel flow electrochemical reactors to develop novel electrosynthetic procedures that are of general interest to the pharmaceutical sector, with the objective to accelerate the transfer of the technology into industrial laboratories. The specific processes to be investigated as part of the CASE award are:
Application of flow electrosynthesis to the oxidative transformation of functional groups common in pharmaceutical intermediates: One of the most common reactions in pharmaceutical manufacturing is the synthesis of amides. Most methods available to achieve this transformation either use hazardous and corrosive intermediates, or generate copious waste. We propose a novel electrochemical transformation of aldehydes to amides catalysed by N-heterocyclic carbenes.
Protecting groups are commonly encountered in laboratory synthesis.
However, conditions required for their chemical cleavage employ excess amounts of toxic reagents. We will develop a general flow electrochemical oxidative removal of protecting groups (para-methoxybenzyl and
para-methoxyphenyl) commonly used for alcohols, carboxylic acids and amines.
Application of flow electrosynthesis to the oxidative transformation of functional groups common in pharmaceutical intermediates: One of the most common reactions in pharmaceutical manufacturing is the synthesis of amides. Most methods available to achieve this transformation either use hazardous and corrosive intermediates, or generate copious waste. We propose a novel electrochemical transformation of aldehydes to amides catalysed by N-heterocyclic carbenes.
Protecting groups are commonly encountered in laboratory synthesis.
However, conditions required for their chemical cleavage employ excess amounts of toxic reagents. We will develop a general flow electrochemical oxidative removal of protecting groups (para-methoxybenzyl and
para-methoxyphenyl) commonly used for alcohols, carboxylic acids and amines.
People |
ORCID iD |
| Richard Brown (Primary Supervisor) | |
| Alexander Teuten (Student) |
Studentship Projects
| Project Reference | Relationship | Related To | Start | End | Student Name |
|---|---|---|---|---|---|
| EP/R513325/1 | 01/10/2018 | 30/09/2023 | |||
| 1796263 | Studentship | EP/R513325/1 | 01/10/2016 | 29/12/2020 | Alexander Teuten |
| Description | The electrochemical deprotection of the 4-methoxybenzyl (PMB) and Trimethylsilyl methylene (TMS-CH2) protecting group from nitrogen containing compounds has been carried out, with good to excellent yields on 15 substrates, using sustainable methodology that paves the way for industry to utilise. |
| Exploitation Route | This work is near completion, little input is needed. The work may be extended to other protecting groups, or into novel cyclisation reactions that have emerged from this methodology, which could be put to use by other members of the research group, opening up the opportunity for further PHD studentships in the field of electrosynthesis. |
| Sectors | Agriculture, Food and Drink,Chemicals,Pharmaceuticals and Medical Biotechnology |
| Description | Royal Society Summer Science Exhibition |
| Form Of Engagement Activity | Participation in an activity, workshop or similar |
| Part Of Official Scheme? | No |
| Geographic Reach | International |
| Primary Audience | Public/other audiences |
| Results and Impact | The Universities of Bristol, Nottingham and Southampton exhibited at the Royal Society Summer Science Exhibition. The exhibit was "Green Light for Chemistry". This is one of the premier engagement activities, reaching all walks of life. The exhibit included practical demonstrations of electrochemistry, and reactors. The PhD student (Alex Teuten) and PhD supervisor (Richard Brown) attend the event over more than 5 days. The goal was to communicate how good reactor design together heat, light and electricity could contribute towards more sustainable manufacturing of chemicals in the future. The exhibit had excellent feedback. |
| Year(s) Of Engagement Activity | 2019 |
| URL | https://www.nottingham.ac.uk/news/summer-science-green-chemistry |