Development and pilot scale implementation of safe aerobic Cu/TEMPO oxidation in a batch reactor

Lemaitre, Sylvain; Romain, Anne-Lise; Bariere, François; Craquelin, Anthony; Copin, Chloé; Jean, Alexandre

doi:10.1039/d3gc00579h

Cited by 6 publications

(2 citation statements)

References 148 publications

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“…Reagent-based manipulation of the oxidation state of certain bonds in active pharmaceutical ingredient (API) manufacture is less desirable due to the increase in concession steps, decrease in atom economy, and general increase the product mass intensity. − Moreover, many stoichiometric oxidants − and reductants − can pose serious safety risks and/or complicate downstream isolations due to byproduct contamination and increase the burden on isolations due to mass intensity. Replacing hazardous, mass-inefficient oxidants/reductants with controlled electrochemical reactions will enable a more versatile design of API syntheses and engage renewable feedstocks.…”

Section: Introductionmentioning

confidence: 99%

A Scalable Solution to Constant-Potential Flow Electrochemistry

Griffin,

Harper,

Velasquez Morales

et al. 2024

Org. Process Res. Dev.

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The burgeoning interest in new electrochemical methods holds promise to provide a plethora of strategic disconnections for pharmaceutical compounds that are safer, less wasteful, and more streamlined than traditional chemical strategies. The use of organic electrochemistry in the commercial production of pharmaceuticals is exceedingly rare due to the lack of a modular infrastructure. Herein we describe the use of cascading continuous stirred tank reactors with individual cell potential control applied over reaction "stages" which demonstrate a balance between high selectivity and throughput necessary for electrochemistry to be a viable strategy in the pharmaceutical space. Using the high degree of control of cell potential afforded by this reactor design, a 1 kg demonstration was achieved in 9 h with high selectivity and yield (2.6 kg/day throughput).

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Section: Introductionmentioning

confidence: 99%

A Scalable Solution to Constant-Potential Flow Electrochemistry

Griffin,

Harper,

Velasquez Morales

et al. 2024

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…The use of redox manipula ons in the manufacture of ac ve pharmaceu cal ingredients (APIs) is o en avoided due to the large amounts of chemical waste generated for a transforma on that doesn't significantly increase the molecular complexity. [22][23][24] Moreover, many stoichiometric oxidants [25][26][27][28] and reductants [29][30][31][32] can pose serious safety risks and/or complicate downstream isola ons. Replacing hazardous, mass-inefficient oxidants/reductants with controlled electrochemical reac ons will enable more versa le design of API syntheses and engage renewable feedstocks.…”

mentioning

confidence: 99%

A Scalable Solution to Constant Potential Flow Electrochemistry

Griffin,

Harper,

Velasquez

et al. 2023

Preprint

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The burgeoning interest in new electrochemical methods holds promise to provide a plethora of strategic disconnections for pharmaceutical compounds, which are safer, less wasteful, and more streamlined than traditional chemical strategies. The use of organic electrochemistry in the commercial production of pharmaceuticals is exceedingly rare due to the lack of a modular infrastructure. Herein, we describe the use of cascading continuous-stirred tank reactors (CSTRs) with individual cell potential control applied over reaction ‘stages’ which demonstrate a balance between high selectivity and throughput necessary for electrochemistry to be a viable strategy in the pharmaceutical space. Using the high degree of control of cell potential afforded by this reactor design, a 1 kg demonstration was achieved in 9 hours with high selectivity and yield (2.6 kg/day throughput).

show abstract