JOURNAL OF ORGANIC CHEMISTRY, v.71, no.1, pp.413 - 415
Abstract
The basicity of an amine has a great impact on physicochemical properties and pharmacokinetics. To attenuate the basicity of morpholine, a bicyclic amine was designed and synthesized with the introduction of an additional β-oxygen. A transannular cyclization and reduction of a bridgehead α-chloro amine functionality produces the topographically unusual amine (pKa = 6.7) in good yield.