Will LiAlH4/THF work for reducing a secondary amide? Ive found most books say that it does not always work and I cant find very many references using
LiAlH4.
Selective Reduction of Secondary Amides to Amines in
the Presence of Tertiary Amides Byung H. Lee* and Michael F. Clothier Tetrahedron Letters 40 (1999) 643-644
Abstract:
Secondary amides activated with a Cbz group can be reduced to their corresponding hemiaminals using lithium borohydride. Hydrogenation then removes
the Cbz and hydroxyl groups to produce the related amine.
Tertiary amides are not affected.
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