Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 25, Issue 1, Pages 148-156Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00361
Keywords
homopiperazine; continuous-flow; Schmidt; oxaziridine; photochemical; microreactor
Categories
Funding
- CRUK Manchester Institute Drug Discovery Unit [C5759/A12328]
- Cancer Research UK [C309/A11566, C309/A8274, C107/A10433]
- Wellcome Trust [1003X, 103021/Z/13/Z, 100282/Z/12/Z]
- Wellcome Trust [103021/Z/13/Z] Funding Source: Wellcome Trust
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The scale-up of a chiral bicyclic homopiperazine of pharmaceutical interest was improved using continuous-flow chemistry, with enhancements in outcome and safety profile of a key batch ring-expansion step. The selectivity of nitrogen insertion for the ring expansion was enhanced via an alternative photochemical oxaziridine rearrangement under mild conditions, leading to the first photochemical scale-up of a homopiperazine in a simple and efficient flow reactor.
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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