Merrell Dow Pharmaceuticals

Laura J Creemer

Peter Biagio Anzeveno

Paul T Angell

Paul S Liu

John K Daniel

The present invention relates to an efficient new route for the preparation of (+)-nojirimycin and (+)-1-deoxynojirimycin which involves the stereoselective reductive amination of 1,2-O-isopropylidene-5-oxo-.alpha.-D-glucuronolactone. The reductive amination uses particular oximes of the 5-oxo compound.

Process for the preparation of nojirimycin and related compounds

Castanospermine is prepared by starting from 5-(t-BOC)amino-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucuronolactone. Two additional carbons are added to the starting material using ethyl acetate and a strong base and the resulting cyclic hemiketal is subjected to a series of reductions, with intervening removal of protecting groups, to give the castanospermine. A substituted hydroxypyrrolidinone and a substituted hydroxypyrrolidine serve as intermediates in the process.

Intermediates in a process for the preparation of castanospermine

Process for the preparation of castanospermine

A procedure for the mild conversion of a carbonitrile to the corresponding carboxylic acid by first using trifluoroacetic acid in the presence of a catalytic amount of mercuric ion followed by oxidative hydrolysis with dinitrogen tetroxide is described herein. The use of this procedure in the preparation of 1,3,4,5-tetra-O-benzoyl-2,6-dideoxy-2,6-imino-D-glycero-L-gulo-heptitol hydrochloride is also described here.

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Indianapolis, IN, United States of America

Laura J Creemer