Zuclomiphene salts and crystalline forms thereof

A process for the preparation of a solid that is isomerically enriched in zuclomiphene of Formula (1-A) relative to enclomiphene of Formula (1-B):

• or a salt thereof, the process comprising:
• (i) crystallizing and isolating a solid, from a mixture comprising enclomiphene binaphthyl hydrogen phosphate salt and zuclomiphene binaphthyl hydrogen phosphate salt in a solvent (S1), that is isomerically enriched in the enclomiphene binaphthyl hydrogen phosphate salt to afford a first solution;
• and either:
• (ii-a) crystallizing and isolating a solid from the first solution that is isomerically enriched in the zuclomiphene binaphthyl hydrogen phosphate salt;
• or
• (ii-b)(a) treating the first solution with a base to liberate binaphthyl phosphate salt and removing it from the first solution to afford a second solution;
• (b) treating the second solution with oxalic acid;
• and
• (c) crystallizing and isolating a solid from the second solution that is isomerically enriched in the zuclomiphene oxalate salt;
• wherein the mixture is enriched in enclomiphene binaphthyl hydrogen phosphate salt relative to zuclomiphene binaphthyl hydrogen phosphate salt.