Lithium aluminum hydride-N-methylpyrrolidine complex. 1 Synthesis and reactivity of lithium aluminum hydride-N-methylpyrrolidine complex. An air and thermally stable reducing agent derived from lithium aluminum hydride

Article abstract of DOI:10.1016/S0040-4039(00)76746-3

A 1:1 lithium aluminum hydride-N-methylpyrrolidine complex (LAHNMP), obtained by the reaction of lithium aluminum hydride with N-methylpyrrolidine, is a powerful reducing agent, comparable to lithium aluminum hydride in its reducing properties. LAHNMP reduces esters, lactones, anhydrides and carboxylic acids to the corresponding alcohols. Test reductions show that LAHNMP also reduces a wide range of functional groups, including amides, epoxides, oximes, nitriles, nitro compounds and halides. LAHNMP can be safely transferred in air with the use of a plastic spatula and used in an open container without the need for an inert atmosphere, provided that hydrogen is not evolved during the reduction.