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

Michael Brown | Zendy; Mohammed Aljarah | Zendy; Hannah Asiki | Zendy; Leo Leung | Zendy; Deborah A. Smithen | Zendy; Natalie A. Miller | Zendy; Gábor Németh | Zendy; Lawrence Davies | Zendy; Dan NiculescuDuvaz | Zendy; Alfonso Zambon | Zendy; Caroline J. Springer | Zendy

Open Access

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

Author(s) -

Michael Brown,

Mohammed Aljarah,

Hannah Asiki,

Leo Leung,

Deborah A. Smithen,

Natalie A. Miller,

Gábor Németh,

Lawrence Davies,

Dan NiculescuDuvaz,

Alfonso Zambon,

Caroline J. Springer

Publication year - 2020

Publication title -

organic process research and development

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.904

H-Index - 109

eISSN - 1520-586X

pISSN - 1083-6160

DOI - 10.1021/acs.oprd.0c00361

Subject(s) - chemistry , bicyclic molecule , oxaziridine , ring (chemistry) , selectivity , stereochemistry , continuous flow , photochemistry , computational chemistry , medicinal chemistry , organic chemistry , catalysis , physics , mechanics

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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