Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives thereof

US5151519A · kind A · utility

Assignee

• G.D. Searle LLC · US

Inventors

• James R. Behling · Lindenhurst, US
• Payman Farid · Deerfield, US
• Ish Khanna · Vernon Hills, US
• John R. Medich · Highland Park, US
• Mike Prunier · Vernon Hills, US
• Mike G. Scaros · Arlington Heights, US
• Richard M. Weier · Lake Bluff, US

Key dates

• Filing date: May 7, 1990
• Grant date: Sep 29, 1992
• Expiry date: May 7, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/20
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives of the formula: ##STR1## wherein R is hydrogen, alkyl of 1 to 13 carbon atoms, and aralkyl wherein alkyl is a lower alkyl of 2 to 6 carbon atoms, and aryl is phenyl, unsubstituted or substituted with lower alkyl of 1 to 6 carbon atoms, halo, lower alkoxy of 1 to 4 carbon atoms or thio lower alkyl of 1 to 4 carbon atoms by the steps of: treating L-sorbose with 2,2-dimethoxypropane to yield 1,2:4,6-di-O-(1-methylethylidene)-.alpha.-L-sorbanose; treating the compound with sulfuric acid in a solvent to produce 1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; consecutively treating with sulfonyl chloride and with an amine to yield 6-(substituted amino)-6-deoxy-1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; adsorbing the compound on an ion exchange resin and hydrogenating to produce compounds of the above formula.