Schering Aktiengesellschaft

Hans Peter Lorenz

Gerhard Sauer

Ulrich Eder

Rudolf Wiechert

Gregor Haffer

Wolfgang Kehr

Helmut Dahl

Reinhard Horowski

Jurgen Ruppert

Compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein R.sub.1 is alkyl of 2-6 carbon atoms, ##STR2## n is 1, or 2, m is 0 or 1,

(Erolinyl)-N,N-diethylurea derivatives, and their preparation and use

Bicycloalkanes of the formula ##STR1## WHEREIN N IS THE INTEGER 1 OR 2; R is methyl or ethyl, and X and Y collectively are a free or ketalized oxo group or X is a hydrogen atom and y is a free, etherified or esterified hydroxy group, are produced by hydrogenating a compound of the formula ##STR2## WHEREIN N, R, X, and Y have the values given above and Me is an alkali metal atom, in an aqueous solution with hydrogen and a palladium-, platinum- or rhodium-containing hydrogenation catalyst. The corresponding free acid is obtained by acidifying the reaction mixture and isolating the reaction product.

Process for the preparation of bicycloalkane derivatives

Bicycloalkanes useful as intermediates in the total synthesis of steroids of the formula ##STR1## WHEREIN N IS THE INTEGER 1 OR 2; R.sub.1 is lower-alkyl; X is free or ketalized carbonyl or free, esterified or etherified hydroxymethylene; and Y is --SO.sub.2 --R.sub.2 or --C(Z)(R.sub.3)--R.sub.4 wherein R.sub.2 is alkyl, aryl or aralkyl R.sub.3 is H or lower-alkyl, R.sub.4 is alkoxycarbonyl or acyl and Z is lower-alkoxycarbonyl, lower acyl, lower alkylsulfinyl or lower-alkylsulfonyl, are produced by the steps of hydrogenating a compound of the formula ##STR2## AND CONDENSING THE THUS-PRODUCED RING SATURATED COMPOUND WITH A SALT OF THE FORMULA C(Z)(R.sub.3)R.sub.4 .sup.-Me.sup.+ wherein n, X, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and Z have the values given above.

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Berlin, Germany

Hans Peter Lorenz