Schering Aktiengesellschaft

Helmut Hauser

Rudolf Wiechert

Gerhard Sauer

Gregor Haffer

Ulrich Eder

Juergen Ruppert

Jurgen Ruppert

Bicycloalkane derivatives of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is lower alkyl, Acyl is alkanoyl, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is acyl or phenyl optionally substituted with lower alkoxy, benzyloxy or alkanoyloxy; and Z is nitro, lower alkoxycarbonyl, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or sulfinic acid, followed if desired by oxidation and optional salt condensation.

Novel bicycloalkane derivatives and the production thereof

Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is aliphatic acyl and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

Bicycloalkane derivatives

Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or a free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is aryl or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is phenyl optionally substituted with lower alkoxy or benzyloxy, and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl, are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is free or ketalized carbonyl or a free, esterified, or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, aryl, or aralkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is alkoxycarbonyl, or acyl or phenyl optionally substituted with lower alkoxy or benzyloxy- or acyloxy; and Z is nitrile, nitro, lower alkoxycarbonyl, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

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Unna, Germany

Helmut Hauser