Improvement on the Synthesis of Primary Amino Sugar Derivatives <i>via</i><i>N</i>-Benzyl Intermediates

• 作者: Felicia D’Andrea Giorgio Catelani Marco Bonanni Massimo Corsi Roberto Bianchini Tiziana Gragnani
• 来源期刊: 有机化学国际期刊(英文)
• 学科: 化学
• 关键词: Amino Sugars NUCLEOPHILIC Substitution BENZYLAMINE PRIMARY TOSYLATES
• 年，卷（期）: yjhxgjqkyw_2013,（3）
• 页码范围: 41-48
• 页数: 8页
• 分类号: O6

摘要

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.