An unexpected Hoffmann elimination during the alkylation of dihydrotetrabenazine

作     者：Zhang Yu Yao Hao Zhang Huan Ming Sheng Xiao Ming Wu Hong Bin Sun 

作者机构：Center for Drug DiscoveryCollege of PharmacyChina Pharmaceutical UniversityNanjing 210009China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报(英文版))

年 卷 期：2010年第21卷第11期

页      面：1334-1337页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by the "111 Project" from the Ministry of Education of China and the State Administration of Foreign Expert Affairs of China(No.111-2-07) 

主　　题：Tetrabenazine Dihydrotetrabenazine Alkylation Hoffmann elimination 

摘      要：Dihydrotetrabenazine(DTBZ) is the major pharmacologically active form of tetrabenazine(TBZ),which was approved by FDA for the treatment of chorea associated with Huntington’s disease(HD).An unexpected Hoffmann elimination was observed during the treatment of DTBZ with sodium hydrogen and alkyl halides,leading to the formation of both eliminated products(major) and hydroxyl-alkylated products(minor).