AMINOBOROHYDRIDES .8. A FACILE REDUCTION OF ALIPHATIC AND BENZYLIC AZIDES TO THE CORRESPONDING AMINES IN HIGH-YIELD AND PURITY USING LITHIUM N,N-DIMETHYLAMINOBOROHYDRIDE

被引:40
作者
ALVAREZ, SG [1 ]
FISHER, GB [1 ]
SINGARAM, B [1 ]
机构
[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064
关键词
D O I
10.1016/0040-4039(95)00341-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lithium N,N-dimethylaminoborohydride (LiMe(2)NBH(3)) reduced both 3 alpha-azidocholest-5-ene and 3 beta-azidocholest-5-ene in air to give the corresponding 3 alpha-aminocholest-5-ene and 3 beta-aminocholest-5-ene in 98% isolated yields. Aliphatic and benzylic azides were also reduced with LiMe(2)NBH(3) to give the corresponding amines in isolated yields ranging from 85 to 98%. The reductions were complete in 1-3 hours and required only a simple acid-base extraction to isolate the desired amines.
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页码:2567 / 2570
页数:4
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