Reduction of amide carbonyl group and formation of modified amino acids and dipeptides

An expeditious, practical, and mild method for the reduction of amides to amines is reported. The procedureis based on the activation of amides with titanium tetrachloride followed by reduction with lithiumaluminum hydride. The reducing system can be applied to the reduction of tertiary and secondary amidesgiving the corresponding amines in good yields. The protocol was also extended to the reduction ofamides of Na-protected amino acid and dipeptides. The corresponding 1,2 diamines and diaminoalcoholswere produced in high yields and with retention of configuration at the chiral centers.