Patent ID: 7135570

Claim:
A process for synthesizing an enantiomer of a primary amino-substituted fused bicyclic ring of formula IX comprising: a) forming the Schiff base of a keto group located on ring B of the fused bicyclic ring by reacting it with an enantiomerically-pure primary amine chiral auxiliary R*NH 2 of the formula X to produce the corresponding enantiomerically-pure imine of the fused bicyclic ring; b) diastereoselectively reducing the imine to produce the corresponding enantiomerically-pure secondary amine on the fused bicyclic ring; and c) removing the chiral auxiliary R* to form the enantiomer of the primary amino-substituted fused bicyclic ring; wherein ring A is a heteroaromatic 5- or 6-membered ring, P is a nitrogen atom, sulfur atom or oxygen atom; ring B is a 5- or 6-membered cycloalkyl or heterocycloalkyl; wherein NH 2 is located at a position on ring B; and R 2 is located at any other hydrogen position on the fused bicyclic ring; wherein m is 0–4; R 2 is selected from the group consisting of halo, nitro, cyano, carboxylic acid, alkyl, alkenyl, cycloalkyl, hydroxyl, thiol, a protected amino, acyl, carboxylate, carboxamide, sulfonamide, an aromatic group and a heterocyclic group; and R 4 , R 5 , and R 6 are each different and selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, and a 5- or 6-membered aromatic ring; and at least one of R 4 , R 5 , or R 6 is a 5- or 6-membered aromatic or heteroaromatic ring.