Chlorosulfamic acid → Estrone sulfamate

Participants

Reaction Steps

Sulfamoylation is the key step in the synthesis of 17β-Hydroxyestra-1,3,5(10)-trien-3-yl sulfamate, a potent estrogen after oral administration. 17-Oxo-1,3,5(10)-triene-3-ol (estrone) is reacted with sulfamoyl chloride to yield 17-Oxoestra-1,3,5(10)-trien-3-yl sulfamate, which is in turn converted to 17β-Hydroxyestra-1,3,5(10)-trien-3-yl sulfamate by means of a complex hydride reagent. According to this invention, the preferred complex hydride reagent is sodium borohydride.

Provenance & Evidence