Nitrogenous analogues of steroids—VII

Add time:08/03/2019    Source:sciencedirect.com

The synthesis of 3β-hydroxy-5-azacholestane (10a) from cholesterol (1) is described. B-norcholest-4-ene-3-one (2) obtained from 1, was reduced to carbinol 3a. The aeetyl derivative (3b) of the latter, after ozonolysis and methylation, afforded the methyl ester of 3β-acetoxy-4,5-seco-5-keto-B-norcholestan-4-oic acid (5b). Beckmann rearrangement of the oxime 6, obtained from 5b, yielded lactam 7b, which was hydrolysed to hydroxyacid 7a; the latter, after N-cyclization and LAH reduction, afforded 3β-hydroxy-5-azacholestane (10a).

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