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 language | English |
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Journal | Organic Process Research & Development |
Early online date | 15 Oct 2020 |
DOIs | |
Publication status | E-pub ahead of print - 15 Oct 2020 |