Toward the Scale-Up of a Bicyclic Homopiperazine via Schmidt Rearrangement and Photochemical Oxaziridine Rearrangement in Continuous-Flow

Michael Brown, Mohammed Aljarah, Hannah Asiki, Leo M. H. Leung, Deborah A. Smithen, Natalie Miller, Gabor Nemeth, Lawrence Davies, Dan Niculescu-duvaz, Alfonso Zambon, Caroline Springer

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
JournalOrganic Process Research & Development
Early online date15 Oct 2020
DOIs
Publication statusE-pub ahead of print - 15 Oct 2020

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