The goal of this research project is to prepare the 1,2-amino alcohol from the epoxide diethyl (hydoxy(oxiran-2-yl)methyl)phophonate 1  which was synthesized from the epoxidation of diethyl (1-hydroxyallyl)phosphonate. Epoxide 1  was purified on a C-18 column using 50/50 methanol/water as the eluent. Analysis of the epoxide utilized 1H-NMR, 13C-NMR, 31P-NMR and IR spectroscopy. Nucleophiles such as benzyl isocyanate can open the epoxide ring to form an oxazolidinone 2  which could be hydrolyzed to form the 1,2-amino alcohol diethyl (2-amino-1,3-dihydroxypropyl)phosphonate 3  . The oxazolidinone and amino alcohol products from the nucleophilic addition and hydrolysis reactions, respectively, will be analyzed using 1H-NMR, 13C-NMR and 31P-NMR. Potentially, the amino alcohol product could be significant for treating medical conditions such as Giardia lamblia. 

Development of new methods towards the synthesis of biologically relevant phosphonates

247th National Meeting (2014)

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