Kaidi Tian, Tingna Cai, Zedong Zhu, Kai Cheng, Lemao Yu, Yong Li
{"title":"Mechanochemical deprotection of t-butoxycarbonyl (Boc) group using basic alumina","authors":"Kaidi Tian, Tingna Cai, Zedong Zhu, Kai Cheng, Lemao Yu, Yong Li","doi":"10.1039/d4ob01091d","DOIUrl":null,"url":null,"abstract":"A solvent-free, operationally simple, and chemoselective mechanochemical method for <em>t</em>-butoxycarbonyl (Boc) deprotection is described. In a planetary ball mill, <em>N</em>-Boc groups from protected heterocycles, amides, and anilines, as well as <em>O</em>-Boc groups from carbonates, can be removed selectively, using basic alumina. This high-yielding protocol avoids tedious extraction and column chromatography.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9000,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01091d","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A solvent-free, operationally simple, and chemoselective mechanochemical method for t-butoxycarbonyl (Boc) deprotection is described. In a planetary ball mill, N-Boc groups from protected heterocycles, amides, and anilines, as well as O-Boc groups from carbonates, can be removed selectively, using basic alumina. This high-yielding protocol avoids tedious extraction and column chromatography.