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Synthesis 1987; 1987(12): 1108-1110
DOI: 10.1055/s-1987-28186
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Highly Selective Amination of 1-Primary, 3-Secondary 1,3-Alkanediols. A New Approach to 3-Aminoalkyl 4-Nitrobenzoates

Tadeusz Gajda*
  • *Institute of Organic Chemistry, Technical University (Politechnika), Żwirki 36, PL-90-924 Łódź, Poland
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Publikationsdatum:
20. August 2002 (online)

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1-Primary, 3-secondary 1,3-alkanediols can be selectively aminated at C-1 via OH/NH2 exchange by reaction with diethyl N-Boc-phosphoramidate in ether using triphenylphosphine/diethyl diazenedïcarboxylate as condensing agent, and treatment of the resultant diethyl N-Boc-N-(3-hydroxyalkyl)phosphoramidates with 4-nitrobenzoyl chloride/pyridine, followed by dephosphorylation with hydrogen chloride in ethyl acetate. The reaction sequence affords the hydrochlorides of 3-aminoalkyl 4-nitrobenzoates in good yields.