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    Toward the scale-up of a bicyclic homopiperazine via schmidt rearrangement and photochemical oxaziridine rearrangement in continuous-flow

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    Authors
    Brown, Michael
    Aljarah, Mohammed
    Asiki, H.
    Leung, Leo M H
    Smith, Deborah A
    Nemeth, G.
    Davies, L.
    Niculescu-Duvaz, Dan
    Zambon, A.
    Springer, Caroline
    Affiliation
    Drug Discovery Unit, Cancer Research UK Manchester Institute, University of Manchester, Alderley Park, Macclesfield SK10 4TG
    Issue Date
    2021
    
    Metadata
    Show full item record
    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.
    Citation
    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.
    Journal
    Organic Process Research and Development
    URI
    http://hdl.handle.net/10541/623844
    DOI
    10.1021/acs.oprd.0c00361
    PubMed ID
    33679122
    Additional Links
    https://dx.doi.org/10.1021/acs.oprd.0c00361
    Type
    Article
    Language
    en
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.oprd.0c00361
    Scopus Count
    Collections
    All Paterson Institute for Cancer Research

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