Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 17α-Acetoxy-6-chloro-2α, 3β-dihydroxy-4, 6-pregnadien-20-one, a Metabolite of Chlormadinone Acetate
阿部 達也, 神戸川 明
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1973 年 21 巻 6 号 p. 1295-1299

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For the purpose of identifying a urinary metabolite of 17α-acetoxy-6-chloro-4, 6-pregnadiene-3, 20-dione (I, chlormadinone acetate) in the rabbit, 17α-acetoxy-6-chloro-2α, 3β-dihydroxy-4, 6-pregnadien-20-one (V), which was found to be identical with the metabolite, was synthesized from I. The starting material (I) was converted to the 2α-and 2β-acetoxy compounds (II and III) on heating with lead tetraacetate in acetic acid. When II and III were reduced with sodium borohydride in anhydrous isopropanol, two 2, 3-dihydroxy compounds (V and VI) were produced. These two diols were found to be 2α, 3β-diol (V) and 2β, 3β-diol (VI), It was also found that both diols formed acetonides. 17β-acetoxy-4-androstene-2α, 3β-diol (XIII) could be also transformed into the acetonide.
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© The Pharmaceutical Society of Japan
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