Reduction of certain steroidal 19-sulfonic esters with metal hydrides

For biosynthetic studies we required steroids labeled with 2H and 3H at C 19. The isotopic hydrogens could be introduced sequentially by stepwise reduction of appropriate 19 oxygenated substrates. The key step of the projected sequence was the conversion of the C10 hydroxymethyl to a methyl. The approaches via the hydrogenolysis of steroidal 19 sulfonic esters with metal hydrides was explored and is described. Under conditions tested only 1-2% of the needed C 10 methyl steroids were formed.