Simple production of oestriol from 1,3,5(10),16-oestratetraene derivative

摘要

A process is disclosed for preparing 16 alpha -hydroxy-estra-1,3,5(10)-triene derivatives having the general formula (I), in which R1 stands for a hydrogen atom, an alkyl group with maximum 4 carbon atoms, a benzyl group or an acyl group with maximum 8 carbon atoms; and X and Y represent together an oxo group or X stands for a hydroxyl group and Y for a hydrogen atom. This process is characterised in that an estra-1,3,5(10),16-tetraene derivative is converted by means of peracids into a 16 alpha ,17 alpha -epoxide, which is split by means of mineral acids or converted by means of a reagent which supplies bromine cations into the corresponding 16 alpha -bromine derivative, which is converted into the 16 beta -bromine derivative. The bromine is replaced by an hydroxyl group and if required the thus obtained 16 alpha -hydroxy-1,3,5(10)triene-17-one derivative is reduced by means of sodium hydroboron in the presence of a strong aqueous buffer solution with a pH value from 5 to 6.5 into the corresponding 16 alpha ,17 beta -trihydroxy-estra-1,3,5(10)-triene derivative.