Sodium Hydroxide → N-Formyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

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Reaction Steps

A mixture of estrone methyl ether (14.2 g) and 2-(2-aminoethyl)-pyridine(24 ml, 24.4 g) is stirred and cooled in an ice bath. To this mixture, formic acid (97-98%, 11.5 ml) is added in portions. The mixture is then heated in an oil bath (180°-190° C. bath temp.) for 24 hours. The mixture is poured onto ice, treated with NaOH, and extracted with methylene chloride (3×). The extracts are dried (Na2SO4), filtered, and concentrated to give a solid. The solid is crystallized from methylene chloride-hexane to give crystals. Recrystallization from methylene chloride-acetone gives the title compound, mp 252°-253° C. preceded by yellowing. (PLA2-, diabetes)

Provenance & Evidence