Author(s)

Massimo Corsi, Marco Bonanni, Giorgio Catelani, Felicia D’Andrea, Tiziana Gragnani, Roberto Bianchini

Dipartimento di Chimica, Università di Firenze, Florence, Italy.
Dipartimento di Farmacia, Università di Pisa, Pisa, Italy.

Primary tosylates 1a-d were converted to the corresponding amino species 3a-d. Benzylamine was proved effective for the substitution of tosylates, using acetonitrile (MeCN) as the solvent of choice and citric acid to remove excess of the reagent from crude products 2a-d. Debenzylation was carried out at circa (ca.) atmospheric pressure of hydrogen gas in the presence of acetic acid (AcOH). The method was also demonstrated in a demo batch experiment for the synthesis of compound 3a on a 50 g scale of 1a.

Amino Sugars; Nucleophilic Substitution; Benzylamine; Primary Tosylates

M. Corsi, M. Bonanni, G. Catelani, F. D’Andrea, T. Gragnani and R. Bianchini, "Improvement on the Synthesis of Primary Amino Sugar Derivatives via N-Benzyl Intermediates," International Journal of Organic Chemistry, Vol. 3 No. 3A, 2013, pp. 41-48. doi: 10.4236/ijoc.2013.33A005.