Abstract
The completely assigned 1H and 13C NMR spectra of the title diastereoisomers in solutions of CDCl3 and DMSO-d6 are reported. NOE experiments show that these molecules adopt specific conformations with no rotation about the C-2—N bond in either solvent. In CDCl3, ring A of the steroid is in a twist-boat conformation and an intramolecular hydrogen bond from the 3α-OH to the morpholine N acts as a conformational lock preventing rotation of the morpholine ring. In DMSO-d6 solutions, ring A of the steroid is in a chair conformation and van der Waals contacts with the 19-methyl group prevent free rotation of the morpholine ring. Molecular mechanics calculations produced four structures that account for the experimental data. © 1997 by John Wiley & Sons, Ltd.
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