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.

Improvement on the Synthesis of Primary Amino Sugar Derivatives via N-Benzyl Intermediates

CATELANI, GIORGIO;D'ANDREA, FELICIA;GRAGNANI, TIZIANA;
2013

Abstract

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.
Corsi, M.; Bonanni, M.; Catelani, Giorgio; D'Andrea, Felicia; Gragnani, Tiziana; Bianchini, R.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/307542
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