Imides reduction, metal hydrides

For a review, see Challis Challis, in Zabicky The Chemistry of Amides, Wiley New York, 1970, pp. 795-801. For a review of the reduction of amides, lactams, and imides with metallic hydrides, see Gaylord. Ref. 536. pp. 544-636. For a lisl of reagents, with references, see Ref. 21. pp. 432-433. 

Finally, the regioselection in metal-hydride reduction of unsymmetrically substituted acyclic diesters is not understood [176] here, as well as in the reactions of cyclic anhydrides and imides, the effect of steric hindrance appears to play a minor role. 

The problem is apparently due to some residual aluminum that is hard to remove. If, however, the reduction is carried out in a iV-methylmorpholine solution, followed by addition of potassium tartrate, a pure product can be isolated. A -Methylmorpholine is a good solvent for reductions of various macromolecules with metal hydrides.In addition, the solvent permits the use of strong NaOH solutions to hydrolyze the addition complexes that form. Other polymers that can be reduced in it are those bearing nitrile, amide, imide, lactam, and oxime pendant groups. Reduction of polymethacrylonitrile, however, yields a product with only 70% of primary amine groups. Complete reductions of pendant carbonyl groups with LiAlH4 in solvents other than A -methyl-morpholine, however, were reported. Thus, a copolymer of methyl vinyl ketone with styrene was fully reduced in tetrahydrofuran. ... 

---