Methylamine → 11beta-Fluoro-3-hydroxy-7alpha-[5-(methylamino)hexyl]oestra-1,3,5(10)-trien-17-one

Participants

Reaction Steps

718 mg of methylamine is condensed in a solution of 960 mg of 11β-fluoro-3-hydroxy-7α-(6-iodohexyl)-estra-1,3,5(10)-trien-17-one in 9 ml of anhydrous tetrahydrofuran at −78° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −20° C., it is allowed to come to room temperature to allow excess methylamine to evaporate off. Then, the reaction solution is added to saturated sodium bicarbonate solution, extracted 3 times with ethyl acetate, dried on sodium sulfate and concentrated by evaporation in a vacuum. 763 mg of 11β-fluoro-3-hydroxy-7α-[5-(methyl-amino)-hexyl]-estra-1,3,5(10)-trien-17-one is obtained as a crude product.

Provenance & Evidence