An amide reduction to an amine is an important transformation reaction for the development of pharmaceutical drugs. In the present work, the reduction of modeled amide, N,N-dimethylacetamide using BH3 (borane) or AlH3 (alane) to give N,N-dimethylethanamine...
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An amide reduction to an amine is an important transformation reaction for the development of pharmaceutical drugs. In the present work, the reduction of modeled amide, N,N-dimethylacetamide using BH3 (borane) or AlH3 (alane) to give N,N-dimethylethanamine has been studied using the DFT calculations. The reaction pathways were searched by intrinsic reaction coordinate analysis. Two possible transition states of amide reduction were found. The first transition state is BH3 or AlH3 insertion and the second transition state is the hydrogenation couple with the cleavage of BH2-O-BH2 (or AlH2-O-AlH2) group. Structural, electronic and thermodynamic properties of all species have been reported. The rate determining step is the second step which has the highest activation free energies. All of results point that borane and alane can reduce a modeled amide to form an amine.
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