Diazabicycloalkanes with nitrogen atoms in the nodal positions. 5. Synthesis and some reactions of 2-hydroxymethyl-1,4-diazabicyclo [2.2.2]octane

Article abstract of DOI:10.1007/BF00496614

2-Hydroxymethyl-1,4-diazabicyclo[2.2.2]octane was synthesized by reduction of 1,4-diazabicyclo[2.2.2]octane-2-carboxylic acid or its methyl ester with lithium aluminum hydride in tetrahydrofuran and by hydrolysis or hydrogenation of 2-benzyloxymethyl-1,4-diazabicyclo[2.2.2]octane. Depending on the conditions, 2-hydroxymethyl-1,4-diazabicyclo[2.2.2]octane reacts with methyl iodide to give primarily either a bisquaternary or a monoquaternary derivative. The latter is the only product in its alkylation with methyl esters of benzoic and caproic acids.