Tetrahedron Letters p. 2567 - 2570 (1995)
Update date:2022-08-16
Topics:
Alvarez
Fisher
Singaram
Lithium N,N-dimethylaminoborohydride (LiMe2NHB3) reduced both 3α-azidocholest-5-ene and 3β-azidocholest-5-ene in air to give the corresponding 3α-aminocholest-5-ene and 3β-aminocholest-5-ene in 98% isolated yields. Aliphatic and benzylic azides were also reduced with LiMe2NBH3 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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