Process for the preparation of optically enriched 4-aryl-3-hydromethyl substituted piperidines to be used as intermediates in the synthesis of paroxetine

摘要

PCT No. PCT/GB96/03242 Sec. 371 Date Jun. 29, 1998 Sec. 102(e) Date Jun. 29, 1998 PCT Filed Dec. 30, 1996 PCT Pub. No. WO97/24323 PCT Pub. Date Jul. 10, 1997The subject invention pertains to optically-enriched compounds of formula (1), wherein Ar is a C6-20 aryl group; and R1 and R2 are independently H, alkyl or aryl. The subject invention also pertains to method of preparing these compounds. The subject compounds can be prepared by reduction of the corresponding 1,4-dihydropyridine-3-aldehyde, e.g., using hydrogen an a catalyst. The aldehyde can be prepared by hydrolytic cleavage of an aminal obtainable by the reaction of 3-pyridinecarboxaldehyde and a chiral C-2 symmetric diamine, an then stereoselective introduction of the Ar and COOCHR1R2 groups.