One drawback is its lack of selectivity.

The method consists of activation of amides with TMSCl followed by reduction with LiAlH 4. An expeditious and practical method for the reduction of amides to amines is reported. Note that this reaction is different to that of other C=O compounds which reduce to alcohols
Amides, RCONR'2, can be reduced to the amine, RCH2NR'2 by conversion of the C=O to - CH2 - Amides can be reduced by LiAlH 4 but NOT the less reactive NaBH 4 Typical reagents : LiAlH 4 / ether solvent followedby aqueous work-up. Amides can be converted to 1°, 2° or 3° amines using LiAlH 4. Various amides/lactams including hindered amides and secondary amides gave the corresponding amines in good to excellent yields. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used.

Lithium Aluminum Hydride (LiAlH4) is often the reagent of choice for reducing amides to amines. Reduction of secondary amides to imines and secondary amines has been achieved using low catalyst loadings of readily available iridium catalysts such as [Ir (COE) 2 Cl] 2 with diethylsilane as reductant.


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