A simple and scalable method to prepare 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane

A simple and scalable method for the preparation of a potentially versatile organostannane, 1-aza-5-chloro-5-stannabicyclo[3.3.3]undecane (1), is described. Stannane 1 was prepared by the disproportionation of N(CH2CH2CH2SnBu3)3 and SnCl4 at 70–100°C. This reaction requires the addition of water or an alcohol to proceed efficiently. Under typical conditions, 1 was isolated in 50–55% yield after a simple acid/base extraction sequence.