Toward the Scale-Up of a Bicyclic Homopiperazine via Schmidt Rearrangement and Photochemical Oxaziridine Rearrangement in Continuous-Flow,Organic Process Research & Development

当前位置： X-MOL 学术 › Org. Process Res. Dev. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Toward the Scale-Up of a Bicyclic Homopiperazine via Schmidt Rearrangement and Photochemical Oxaziridine Rearrangement in Continuous-Flow
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2020-10-15 , DOI: 10.1021/acs.oprd.0c00361
Michael Brown _{1,

2} , Mohammed Aljarah _{1,

2} , Hannah Asiki ₂ , Leo M H Leung _{1,

2} , Deborah A Smithen _{1,

2} , Natalie Miller ₂ , Gabor Nemeth ₂ , Lawrence Davies ₂ , Dan Niculescu-Duvaz _{1,

2} , Alfonso Zambon ₂ , Caroline Springer _{1,

2}

Affiliation

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.

中文翻译：

通过施密特重排和光化学氧氮丙啶重排在连续流中放大双环高哌嗪

研究了具有药用意义的手性双环高哌嗪的放大。使用连续流化学改进了通过施密特重排进行的关键批量扩环步骤的结果和安全性。通过在温和条件下进行替代性光化学氧氮丙啶重排，提高了氮插入对环扩展的选择性，当在简单高效的流动反应器中转化为连续流时，首次实现了高哌嗪的光化学放大。

更新日期：2020-10-15

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11