1 research outputs found
An Improved and Enantioselective Preparation of the Telaprevir Bicyclic [3.3.0] Proline Intermediate and Reuse of Unwanted Enantiomer
An
improved, concise, and efficient preparation of the telaprevir
bicyclic [3.3.0] proline intermediate is presented. The key steps,
control points, and the whole process are optimized. The synthesis
of racemic intermediate was accomplished in five steps in above 56%
overall yield up to 100 g scale with only some simple separations
and treatments in the whole process. The new and crucial chiral resolution
of the proline intermediate was systematically studied, and the target
chiral intermediate was obtained in acceptable yield (30%) and excellent
ee value (>99% ee) by a simple washing. The cost of the target
chiral
intermediate and wastes of the whole process were at least doubly
reduced after the effective reuse of the unwanted chiral amino acid
by successful decarboxylation