Estrone → 3-(2-Aminoethyl)estra-1,3,5(10)-trien-17-one

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Reaction Steps

Estrone (5.0 g, 18.5 mmole) was dissolved in 80 mL of anhydrous DMF. Sodium hydride (4.4 g, 185 mmole) was slowly added to the solution to generate reactive phenoxide in situ. Care was taken to avoid rapid evolution of hydrogen gas. 4.3 g (55 mmole) chloroethylamine was added to the solution and the mixture was allowed to react at 60° C. for 4 hrs. The product was precipitated with a large volume of water and the precipitate collected. For purification, the crude solid was dissolved in methylene chloride, and washed with water. Evaporation of methylene chloride yielded 3-aminoethyl estrone which after washing with ethyl ether gave 3.0 g (52%) of product m.p. 140° C. (decomp.), 3-aminoethyl estrone hydrochloride, m.p. 180° C. (decomp.), 1HNMR (ppm): δ3.01 (2,t,CH2CH2NH2), 2.78 (2,t,CH2,CH2NH2), 4.00 (2,t,COCH2).

Provenance & Evidence