Synthesis of (endo) 3,9-Disubstituted Diazabicyclo(3.3.1)nonan-7- amines.

The novel synthesis of a series of 3,9-diazabicyclo[3.3.1]nonan-7-amines (4) is reported via an alane reduction of a key intermediate oxime (8). The stereoselectivity of the reduction is highly dependent on the size of the 3-aza substituent.