P. Lin, N. Maguire, Daniel M. Brown
May 23, 1994
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 3-Bromopropylamine hydrobromide reacts with N -hydroxyphthalimide in the presence of DBU to give, not the expected N -(3-aminopropyloxy)phthalimide, but N -(3-aminooxypropyl)-phthalimide, 6 , formed by an unusual intramolecular rearrangement. Coupling of the pentamethyl-chroman-6-sulphonyl (Pmc) derivatives of 9 and 13 with N -Bpoc-aminopropanol affords a differentially protected 6-oxaspermidine 10 and 6,9-dioxaspermine 14 respectively from which the protecting groups are removed independently.