Patent ID: 6344566
Filing Date: 2002-02-05
Classification: A61K,A61P,C07B,C07D,Y02P

Abstract:
A process for the preparation of N-methyl-N-[(1S)-1-phenyl-2-((3S)-3-hydroxypyrrolidin-1-yl)]ethyl]-2,2-diphenylacetamide or N-methyl-N-[(1R)-1-phenyl-2-((3R)-3-hydroxypyrrolidin-1-yl)]-2,2-diphenylacetamide comprising:a) reacting an (S)- or (R)-enantiomeric form of in whichR is OR1 or SR1, R1 is A, aryl, heteroaryl, Si (R3)3 or COR3, R3 is H, A, aryl or heteroaryl, A is straight-chain or branched alkyl having 1 to 6 C atoms, M is H or an alkali metal, alkaline earth metal, ammonium or alkylammonium cation, with a (3S)-3-hydroxypyrrolidine or (3R)-3-hydroxypyrrolidine of the formula II in whichR2 is H, A, aryl, heteroaryl, Si (R3)3 or COR3 and R3 is H, A, aryl or heteroaryl or with an acid addition salt of the compound of the formula (II), with an acid HCl, HBr, HI, H2SO4, H3PO4 or an organic carboxylic acid,to give a compound of the formula III in which R and R2 having the meanings given above,b) converting the compound of the formula III by reducing it to a compound of the formula (IV) and optionally converting the latter into a corresponding acid addition salt with an acid HCl, HBr, HI, H2SO4, H3PO4 or an organic carboxylic acid, andc) reacting the compound of the formula (IV) thus obtained with an activated carboxylic acid of the formula (V) in whichR4 is F, Cl, Br, I, OA or Oâ€”COâ€”A, to give the compound of the formula (VI) and optionally converting the latter into the associated acid addition salt with HCl, HBr, HI, sulphuric acid, sulphamic acid, nitric acid, phosphoric acid, orthophosphoric acid, or an organic acid,wherein the starting materials employed in stage a) are selected depending on the enantiomer desired as the final product.