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- Attempts to synthesize 3f following reaction condition B furnished hydrocortisone 17-acetate 21-adamantanecarboxylate (m. p. 270–271−; 11: yield). This compound is distinguished from hydrocortisone 21-acetate 17-adamantanecarboxylate (m. p. 110–115∗) by IR and NHR spectral data and its resistance to hydrolytic condition D. Cbviously under these conditions the bulky adamantane substituted reagent preferably attacks the 21-position forcing the 21-acetate group into the 17-position, possibly via a cyclic orthoester-iike intermediate
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