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A general synthesis of 6-azasteroids Johnson, Roy Allen

Abstract

The ozonization of 7-ketocholesteryl acetate has yielded 5-keto-5, 7-seco-6-nor-3-cholesten-7-oic acid, an intermediate useful in the preparation of 6-azacholestane. Catalytic hydrogenation converted this intermediate to 5-keto-5,7-seco-6-norcholestan-7-oic acid which, upon treatment with benzyl amine, gave N-benzyl-6-aza-4-cholesten-7-one. Catalytic reduction of this enol-lactam yielded N-benzyl-6-azacholestan-7-one which was reduced with lithium aluminum hydride to N-benzyl-6-azacholestane. The generality of this route was shown when it was applied to compounds of the androstane series. Ozonization of 3β,17β-dihydroxy-5-androsten-7-one diacetate gave 17β-hydroxy-5-keto-5,7-seco-6-nor-3-androsten-7-oic acid which was hydrogenated catalytically to 17β-hydroxy-5-keto-5,7-seco-6-norandrostan-7-oic acid. This saturated acid ring—closed with benzyl amine to yield 17β-hydroxy-N-benzyl-6-aza-4-androsten-7-one. Catalytic hydrogenation of this enol-lactam gave 17β-hydroxy~N-benzyl-6-azandrostan-7-one which was reduced with lithium aluminum hydride to N-benzyl-6-azaandrostan-17β-ol. A mild chromic acid oxidation converted the alcohol to the keto compound, N-benzyl-6-azaandrostan-17-one.

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