Process for the preparation of 7alpha-alkylated 19-norsteroids

Abstract

Processes useful in the preparation of pharmaceutical compounds such as fulvestrant and processes for the preparation of fulvestrant.

1 - 50 . (canceled) 
   
   
       51 . A process for preparing the compound of the formula (I) 
     
       
         
         
             
             
         
       
       comprising combining the compound of formula (VII) 
     
     
       
         
         
             
             
         
       
       with 4,4,5,5,5-pentafluoropentane-1-ol mesylate at an ambient temperature; 
       combining the obtained reaction mixture with a base in the presence of an organic solvent; and recovering the compound of the formula (I); 
       wherein
 n is an integer ranging from 3 to 14; 
 R 1  is —S—(CH 2 ) 3 CF 2 CF 3 ; 
 R 2  is either hydrogen, C 1-6  alkyl, hydroxyl, protected hydroxy, or halo; 
 R 3  is either hydrogen, C 1-6  alkyl, C 2-6  alkenyl, or C 2-6  alkynyl; 
 R 4  is either hydroxy or C 1-6  acyloxy; 
 R 5  is C 1-6  alkyl; and 
 R 6  is either hydrogen, C 1-6  alkyl, hydroxyl, protected hydroxy, or halo. 
 
     
   
   
       52 . The process of claim  0 , wherein n is 9, R 2 , R 3  and R 6  are hydrogens, R 4  is a acetyloxy and R 5  is methyl. 
   
   
       53 . The process of claim  0 , wherein n is 9, R 2 , R 3  and R 6  are hydrogens, R 4  is acetyloxy and R 5  is methyl. 
   
   
       54 . The process of claim  0 , wherein the base is an alkali metal base. 
   
   
       55 . The process of claim  0 , wherein the base is KOH. 
   
   
       56 . The process of claim  0 , wherein the organic solvent is a C 1-6  alcohol. 
   
   
       57 . The process of claim  0 , wherein the organic solvent is methanol. 
   
   
       58 . The process of any one of claims  0  and  0 , further comprising converting the obtained product to fulvestrant. 
   
   
       59 - 62 . (canceled)