Potassium trimethylsilanolate induced cleavage of 1,3-oxazolidin-2 and 5-ones, and application to the synthesis of (R)-salmeterol

被引：36
|
作者：
Coe, DM [1 ]
Perciaccante, R [1 ]
Procopiou, PA [1 ]
机构：
[1] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 07期
关键词：
D O I：
10.1039/b212454h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and efficient method for the cleavage of 1,3-oxazolidin-5-ones and 1,3-oxazolidin-2-ones utilising potassium trimethylsilanolate in tetrahydrofuran is described. The benzyloxycarbonyl-protecting group is readily removed under the reaction conditions, whereas the N-benzoyl group is stable. A synthesis of (R)-salmeterol exploiting the 2-oxazolidinone ring as a protecting group for the ethanolamine moiety is also described.
引用
收藏
页码：1106 / 1111
页数：6
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