Aminoborohydrides. 8. A facile reduction of aliphatic and benzylic azides to the corresponding amines in high yield and purity using lithium N,N-dimethylaminoborohydride

Article abstract of DOI:10.1016/0040-4039(95)00341-9

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.