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Toward the scale-up of a bicyclic homopiperazine via schmidt rearrangement and photochemical oxaziridine rearrangement in continuous-flow
Brown, Michael Aljarah, Mohammed Asiki, H. Leung, Leo M H Smith, Deborah A Nemeth, G. Davies, L. Niculescu-Duvaz, Dan Zambon, A. Springer, Caroline
Brown, Michael
Aljarah, Mohammed
Asiki, H.
Leung, Leo M H
Smith, Deborah A
Nemeth, G.
Davies, L.
Niculescu-Duvaz, Dan
Zambon, A.
Springer, Caroline
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Abstract
The scale-up of a chiral bicyclic homopiperazine of pharmaceutical interest was investigated. The outcome and safety profile of a key batch ring-expansion step via Schmidt rearrangement was improved using continuous-flow chemistry. The selectivity of nitrogen insertion for the ring expansion was improved via an alternative photochemical oxaziridine rearrangement under mild conditions, which when converted to continuous-flow in a simple and efficient flow reactor allowed the first photochemical scale-up of a homopiperazine.
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Date
2021
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Brown M, Aljarah M, Asiki H, Leung LMH, Smithen DA, Miller N, et al. Toward the Scale-Up of a Bicyclic Homopiperazine via Schmidt Rearrangement and Photochemical Oxaziridine Rearrangement in Continuous-Flow. Org Process Res Dev. 2021;25(1):148-56.