Tetrahedron Letters p. 3605 - 3608 (1994)
Update date:2022-08-11
Topics:
Lin, Paul Kong Thoo
Maguire, Nuala M.
Brown, Daniel M.
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.
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