Selective reduction of secondary amides to amines in the presence of tertiary amides

Article abstract of DOI:10.1016/S0040-4039(98)02509-X

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.