Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±) Tolterodine

A simple synthetic route to access racemic 3,3-disubstituted propylamines in excellent yields (up to 95%) via Lewis acid catalyzed S(N)2-type ring opening of activated azetidines with electron-rich arenes and heteroarenes under mild conditions has been accomplished. The methodology is efficiently used for the racemic synthesis of an antimuscarinic drug, tolterodine, in four steps in 47% overall yield.