A novel method of synthesis of 1-azaadamantane from 1-boraadamantane

Article abstract of DOI:10.1016/0022-328X(91)86035-O

A novel and convenient method for the synthesis of 1-azaadamantane (I) from the 1-boraadamantane-tetrahydrofuran complex (XIII) is described.This is based on an intramolecular reaction of organic azides with organoboron compounds.Treatment of the boron cage compound XIII with iodine and an excess of sodium azide followed by oxidation (H2O2, OH^-) affords 7α-hydroxymethyl-3-azabicyclo<3.3.1>nonane (VII), cyclization of which leads to I in 40percent overall yield.Some new boron cage compounds were also isolated, diazidoborane (XIV) being of particular interest.