ALKYLATION OF N-BOC-1,2,3,4-TETRAHYDROISOQUINOLINES IN THE 1-POSITION AND ITS APPLICATION TO THE SYNTHESIS OF ISOQUINOLINE ALKALOIDS

被引：20
|
作者：
COPPOLA, GM
机构：
[1] Sandoz Research Institute, Chemistry Research Department, Sandoz Pharmaceuticals Corporation, East Hanover, New Jersey, 07936
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 07期
关键词：
D O I：
10.1002/jhet.5570280720
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Boc-protected 1,2,3,4-tetrahydroisoquinolines 2 can be lithiated with t-butyllithium in the presence of N,N,N',N'-tetramethylethylenediamine. Reaction of the anion with alkyl halides provides 1-alkyl N-Boc-1,2,3,4-tetrahydroisoquinolines in 67-71% yield. The protecting group is easily removed in high yield with trifluoroacetic acid. The alkaloids salsolidine (8) and laudanosine (11) were synthesized in racemic form using this method.
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收藏
页码：1769 / 1772
页数：4
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