Toward the scale-up of a bicyclic homopiperazine via schmidt rearrangement and photochemical oxaziridine rearrangement in continuous-flow
Leung, Leo M H
Smithen, Deborah A | |Miller, N.
AffiliationDrug Discovery Unit, Cancer Research UK Manchester Institute, University of Manchester, Alderley Park, Macclesfield SK10 4TG
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AbstractThe 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.
CitationBrown 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.
JournalOrganic Process Research and Development