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Transformed steroids. 118. The geometric isomerism of 20-ethoxycarbonylhydrazones of 3β-hydroxy-16,17α-cyclopropanopregn-5-en-20-one

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In the reaction of the 3β-acetate of 3β-hydroxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (I) with ethoxycarbonylhydrazine in AcOH at 20°C (exposure for up to 6 days), a chromatographically separable equilibrium mixture of the 20Z-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (II), with mp 190–195°C, and the 20E-ethoxycarbonylhydrazone of 3β-acetoxy-3′H-cyclopropano[16,17α]pregn-5-en-20-one (III) with mp 186–193°C (ratio 2:1) is obtained. The geometric isomers obtained are distinguished by IR, PMR, and CD spectroscopy. It has been shown that the observed geometric isomerism takes place via an intermediate enehydrazine form.

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Literature cited

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Additional information

For Communication 117, see [1].

N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 530–533, July–August, 1980.

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Kamernitskii, A.V., Turuta, A.M. & Ngo Tkhi Mai An' Transformed steroids. 118. The geometric isomerism of 20-ethoxycarbonylhydrazones of 3β-hydroxy-16,17α-cyclopropanopregn-5-en-20-one. Chem Nat Compd 16, 383–386 (1980). https://doi.org/10.1007/BF00568373

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  • Hydrazones
  • AcOH
  • Geometric Isomerism
  • HOAc
  • Furostanol