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Solid-phase syntheses ofN-substituted carbamates. Reaction monitoring by gel-phase13C NMR using a13C enriched BAL-linker

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
19
Identifiers
DOI: 10.1016/s0040-4039(02)00564-6

Abstract

Abstract The solid-phase synthesis of N-substituted carbamates using the tris(alkoxy)benzyl (BAL) resin is reported. The incorporation of the primary amine was carried out by reductive amination, which was followed by reaction with an alkyl succinimidyl carbonate prepared in situ from the alcohol and N,N′-disuccinimidyl carbonate (DSC). Final cleavage with trifluoroacetic acid rendered the target compounds. Scope and limitations of these methods are discussed. The reactions were controlled by gel-phase 13C NMR using a 13C enriched BAL resin.

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