Process for the preparation of 7alpha-methylsteroids
OwnerPatrick, Arnoldus, Maria Van Buggenum, Johannes Stoelwinder +1inventors
InventorsPatrick, Arnoldus, Maria Van Buggenum, Johannes Stoelwinder, Martin Ostendorf
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Abstract
The invention relates to a process for the preparation of 7α-methyl hydroxy steroids of the formula I wherein R1 is hydrogen, methyl or C≡CH; R2 is (CH2)nOH, wherein n is 0, 1 or 2; by a copper mediated 1,6-conjugate addition of a Grignard reagent CH3MgX, X being a halogen, to the 4,6-unsaturated 3-ketosteroid of formula II, wherein R1 and R2 are as previously defined, comprising protecting the hydroxy group of the steroid of formula II with a trialkylsilyl group, followed by treating the hydroxy protected steroid with the Grignard reagent. The process of the invention is useful for the production of pharmacologically interesting steroids.
Claims10
A process for the preparation of 7α-methyl steroids of the formula I
- wherein
- R1 is hydrogen, methyl or C≡CH;
- R2 is (CH2)nOH, wherein n is 0, 1 or 2;
- by a copper mediated 1,6-conjugate addition of a Grignard reagent CH3MgX, X being a halogen, to the 4,6-unsaturated 3-ketosteroid of formula II,
- wherein R1 and R2 are as previously defined,
- comprising:
- protecting the hydroxy group of the steroid of formula II with a trialkylsilyl group,
- followed by treating the hydroxy protected steroid with the Grignard reagent CH3MgX.
A compound 21-hydroxy-19-norpregn-4,6-dien-3-one.
Dependencies are inferred from the claim text.