Title of project
Chemistry and Biochemistry
A Three-Step Synthesis of Hydrogenated Tamoxifen
Tamoxifen is an active molecule that is used to treat estrogen-receptor-positive breast cancer in both men and women. Estrogen-receptor-positive (ER+) breast cancer is where the cancer cells’ growth is promoted by the presence of estrogen. Tamoxifen is an antagonist of the estrogen receptors in the breast tissue because it blocks the receptors, preventing cancer growth. Three steps were taken to synthesize hydrogenated tamoxifen. First, 1-phenyl-1-(p-hydroxyphenyl)-2-phenylbut-1-ene was synthesized from 4-hydroxybenzophenone and propiophenone, using THF as a solvent. Then, the product was amino alkylated to synthesize E and Z isomers of tamoxifen, to which it was hydrogenated to produce our final product, hydrogenated tamoxifen. In order to make this process more green 2-methyltetrahydrofuran (2-meTHF) was used in place of THF wherever possible.