Louis Provencher

New efficient pathway for the synthesis of 3-aminoestrone

Abstract 3-Aminoestrone, a non-natural C-18 steroid, was synthesized by the classical and by a new efficient pathway, the latter using benzophenone imine as an ammonia equivalent in the palladium(0)-catalysed amination of estrone-triflate. This methodology circumvents the problems encountered when applying the classical pathway, the poor yield, high reactional temperature and weak purity.

Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of anti-breast cancer agents

Abstract Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.