Synthesis p. 1108 - 1110 (1987)
Update date:2022-08-03
Topics:
Gajda, Tadeusz
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 diazenedicaboxylate 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.
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