Tetrahedron p. 6303 - 6312 (1997)
Update date:2022-08-30
Topics:
Weidner, John J.
Weintraub, Philip M.
Schnettler, Richard A.
Peet, Norton P.
Acylation of hydroxy aromatic compounds with 2-bromo-2-methylpropionamide followed by Smiles rearrangement of the resulting 2-aryloxypropionamide in a one-pot procedure produced the corresponding 2-hydroxy-2-methyl-N-arylpropionamides which can be converted to arylamines by hydrolysis. Particularly important applications of this new process were the conversions of estrone (6) and estradiol (14) to the corresponding 3-aminoestrahriene derivatives 8 and 15, respectively. In addition, an improved Semmler-Wolff procedure is described for the conversion of 19-nortestosterone (22) to 3-aminoestra-1,3,5(10)-uien-17β-ol hydrochloride (26).
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