Synthesis of 11α- and 11β-diethylaminoethyl ethers of 17α-ethynylestradiol

Abstract

The 11α- and 11β-diethylaminoethyl ethers of 17α-ethynylestradol have been prepared from the intermediate alcohols (7a) and (7b) by direct alkylation with 2-N,N-diethylaminoethyl bromide hydrobromide followed by hydrogenolysis, deacetalization, and reaction with lithium acetylide. The two 11-diethylaminoethyl ethers of 17α-ethynylestradiol showed no significant estrogenic, anti-estrogenic, or post-coital activity.