Pyridine → 3-Methoxy-estra-2,5(10)-dien-17-ol

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Reaction Steps

According to the German patent application DD 132,497 3-methoxy-17β-spiro-1′,2′-oxirane-estra-2,5(10)-diene is reacted with an alkali metal cyanide to yield a 17α-cyanomethyl-17β-hydroxy-3-enolether derivative. Then the so obtained compound is hydrolyzed, brominated and dehydrobrominated to furnish the dienogest of formula (I) hi 32% yield. The purity of the obtained dienogest is characterized by the melting point (204-214° C.) and optical rotation ([α]25D=290°, pyridine, c=0.5%). According to the method described in the patent application DD 80,023 3-methoxy-17β-spiro-1′,2′-oxirane-estra-2,5(10)-diene used as starting material can be synthesized by reacting dimethylsulfonium methylide and the 17-oxo derivative obtained by Oppenauer oxidation of the 17-hydroxy group of 3-methoxy-17-hydroxy-estra-2,5(10)-diene of formula (V)—latter synthesized by known methods.

Provenance & Evidence