| abstract |
The invention relates to a process for the enantioselective preparation of tolterodine and analogs and salts thereof comprising the steps of: a) reducing enantioselectively the carbonyl functional group in a compound of formula (II), in which Rl, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulfamoyl or halogen, to form the enantiomerically enriched compound of the formula (IIIa) or (IIIb); b) subjecting the compound of the formula (IIIa) or (IIIb) to a sigmatropic transposition to form a corresponding enantiomerically enriched compound of the formula (IVa) or (IVb); c) subjecting the compound of the formula (IVa) or (IVb) to a Baeyer-Villiger oxidation to form the corresponding enantiomerically enriched compound of the general formula (Va) or (Vb); d) converting the compound of the formula (Va) or (Vb) to form the corresponding enantiomerically enriched tolterodine compound or analogue thereof; and e) optionally converting a compound obtained as a base to a salt thereof, or converting a salt form to the free base form. The formulas (IIIa), (IIIb), (IVa), (IVb), (Va) and (Vb) are specified in the application. The invention also relates to novel starting materials and intermediaries used in the process. |