A COMPARATIVE STRUCTURAL STUDY OF THE STEROID EPIMERS - 17-BETA-AMINO-1,3,5(10)-ESTRATRIEN-3-OL, 17-ALPHA-AMINO-1,3,5(10)-ESTRATRIEN-3-OL AND SOME DERIVATIVES BY H-1-NMR, AND X-RAY-DIFFRACTION ANALYSIS

The epimers 17 beta-amino-1,3,5(10)-estratrien-3-ol and 17 alpha-amino -1,3,5(10)-estratrien-3-ol were synthesized. 17 beta-Amino-1,3,5(10)-e stratrien-3-ol was prepared by catalytic hydrogenation of the estrone- oxime. The 17 alpha-amino epimer was obtained from estradiol, via tosy late, followed by nucleophilic displacement by sodium azide and subseq uent reduction with LiAlH4. They were characterized by spectroscopic m ethods. Determination of the crystal structures of 3-(toluene-4-sulfon yloxy)-17 alpha-azido-1,3,5(10)-estratriene, -sulfonyloxy)-17-alpha-am ino-1,3,5(10)-estratriene hydrochloride, 17 beta-acetylamino-1,3,5(10) -estratriene-3-ol, and 3-acetoxy-17 beta-acetylamino-1,3,5(10)-estratr iene enabled us to characterize the structure of the 17 alpha and 17 b eta amino epimers for the first time. (Steroids 63:556-563, 1998) (C) 1998 by Elsevier Science Inc.