New process

Abstract

The present invention relates to novel resolution methods, which are useful in the preparation of enantiomerically enriched intermediates which in their turn are useful in the prepartion of compounds with a pharmacological effect on the insulin resistance syndrome (IRS). It is such a process that the present inventions sets out to define, and more particularly for the preparation of the (S)-enantioner of certain 2-ethoxy-3-(4-hydroxyphenyl)propanoic acids and derivatives thereof.

1 - 21 . (canceled)  
   
   
       22 . A process for the preparation of a compound of formula VIII  
     
       
         
         
             
             
         
       
     
     wherein Q is a protecting group selected from acetyl and C 1-3  alkyl, and A is OH, a chiral auxiliary group or the group OR p , wherein R p  is a protecting group, and one or more of the hydrogen atoms of the phenyl group are optionally substituted by the equivalent number of halogen atoms, comprising reducing a compound according to formula VI  
     
       
         
         
             
             
         
       
     
     wherein Q is a protecting group or H, and A is OH, a chiral auxiliary group or the group OR p , wherein R p  is a protecting group, and one or more of the hydrogen atoms of the phenyl group are optionally substituted by the equivalent number of halogen atoms, by hydrogenation in the presence of a catalyst.  
   
   
       23 . The process according to  claim 22  in which the catalyst is a chiral catalyst.  
   
   
       24 . The process according to  claim 22  in which Q is methyl.  
   
   
       25 . The process according to  claim 23  in which Q is methyl.  
   
   
       26 . The process according to any one of claims  22 - 25  in which R p  is a protecting group selected from the group consisting of H, benzyl and C 1-3  alkyl.  
   
   
       27 . The process according to claim  1  in which A is a chiral auxiliary group.  
   
   
       28 . The process according to  claim 27  in which the chiral auxiliary group is chosen from the group consisting of terpenes and oxazolidinones.  
   
   
       29 . The process according to  claim 27  or  28  in which the catalyst is palladium on carbon.  
   
   
       30 . The process according to any one of claims  22 - 25 , wherein the one or more halogen atoms of formula VI are selected from the group consisting of chlorine and bromine and any combination thereof.