15.alpha.,-Sulfonyloxy-12.beta.-hydroxypregnanes and process for the preparation thereof
AssigneeSchering Corporation
InventorHans-Gunter Lehmann
Life of this patent
Estimating the term…
Abstract
15.alpha.-Sulfonyl-12.beta.-hydroxypregnanes of the formula ##SPC1## Wherein Ac is lower-acyl and R is alkyl, cycloalkyl, aralkyl or aryl, which are useful as intermediates for the production of digoxigenin, are produced by the selective sulfonic acid esterification of the corresponding 12.beta., 15.alpha.-dihydroxy steroid.
Claims10
A 15.alpha.-sulfonyloxy-12.beta.-hydroxypregnane of the formula ##SPC3##
- wherein Ac is the acyl radical of an alkyl, cycloalkyl, cycloalkylalkyl, carbocyclic aryl or carbocyclic aralkyl hydrocarbon carboxylic acid of up to 8 carbon atoms and R is alkyl of 1-8 carbon atoms, cycloalkyl of 3-8 carbon atoms or carbocyclic aryl of 6-18 carbon atoms.
A compound of claim 1, 12.beta.-hydroxy-15.alpha.-(2',4',6'-trimethylphenylsulfonyloxy)-3.beta.-a cetoxy-5.beta.-pregnan-20-one.
A compound of claim 1, 12.beta.-hydroxy-15.alpha.-tosyloxy-3.beta.-acetoxy-5.beta.-pregnan-20-one .
A compound of claim 1, 12.beta.-hydroxy-3.beta.-acetoxy-15.alpha.-mesyloxy-5.beta.-pregnan-20-one .
A compound of claim 1, 12.beta.-hydroxy-3.beta.-acetoxy-15.alpha.-(naphthalene-2-sulfonyloxy)-5.b eta.-pregnan-20-one.
A compound of claim 1, 12.beta.-hydroxy-3.beta.-acetoxy-15.alpha.-(2,4,6-triisopropylbenzenesulfo nyloxy)-5.beta.-pregnan-20-one.
A process for the production of a 15.alpha.-monosulfonyloxy ester of a 12.beta.,15.alpha.-dihydroxypregnane of the formula ##SPC4##
- wherein Ac is the acyl radical of a hydrocarbon carboxylic acid of up to 8 carbon atoms, which comprises reacting the 3.beta.-acyloxy-12.beta.,15.alpha.-dihydroxy-20-ketopregnane with an organic sulfonic acid chloride, in the presence of the tertiary amine.
Dependencies are inferred from the claim text.