Highly Effective Resolution of 1, 3-Dibenzyl-6-hydroxy-3, 3a, 6, 6a-tetrahydro-1H-furo[3, 4-d]imidazole-2, 4-dione, an Intermediate for Biotin, with Optically Active Amines and Reutilizatin of the Unwanted Epimer

摘要: The direct resolution of (3aRS, 6SR, 6aSR)-1, 3-dibenzyl-6-hydroxy-3, 3a, 6, 6a-tetrahydro-1H-furo[3, 4-d]imidazole-2, 4-dione [(±)-9], a key intermediate for biotin, with optically active amines was examined. Reaction (±)-9 cinchonidine readili gave the salt (4S, 5R)-aldehyde-carboxylic acid (12), acidification which (3aS.6R, 6aR)-9, convertible to biothin. N-alkyl-D-glucamines (14) were also found be effective resolving agents applicable industrial use. Reutilizatin unwanted epimer [(3aR, 6S, 6aS)-9] effected by facile oxidation meso-diacid (3) sodium chlorite.