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US 4,066,674 AGranted
Process for the preparation of 1,3-oxygenated 8.alpha.-estratrienes and novel intermediates obtained therefrom
AssigneeSchering Corporation
InventorsUlrich Eder, Gerhard Sauer, Gregor Haffer, Guenter Neef, Rudolf Wiechert
Life of this patent
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Abstract
Novel 1,3-dialkoxy 8.alpha.-estratriene compounds of the formula ##STR1## WHEREIN R.sub.1 is alkyl of 1-18 carbon atoms, R.sub.2 is alkyl of 1-5 carbon atoms and Ac is alkanoyl of 1-8 carbon atoms, are obtained by a three-step synthesis from a tetrahydroindane-5-one compound.
Claims11
A process for the production of a 1,3-oxygenated-8.alpha.-estratriene optical isomer of the formula ##STR9## wherein R.sub.1 is alkyl or aralkyl of up to 8 carbon atoms, R.sub.2 is alkyl of 1-5 carbon atoms and Ac is alkanoyl of 1-8 carbon atoms, which comprises the steps of:
- a. condensing, in the presence of a deprotonating agent, a compound of the formula ##STR10## wherein R.sub.1 is alkyl or aralkyl of up to 8 carbon atoms and Tos is tosyloxy,
- with a tetrahydroindane-5-one compound of the formula ##STR11## wherein R.sub.2 is alkyl of 1-5 carbon atoms and R.sub.3 is tert.-butyl, tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl or tri-p-xylylsilyl, to produce a condensate of the formula ##STR12## wherein R.sub.1, R.sub.2, and R.sub.3 are as above;
- b. cyclizing the condensate in the presence of a strong acid and a carboxylic acid of 1-8 carbon atoms to an estrapentaene of the formula ##STR13## wherein R.sub.1, R.sub.2, and Ac are as above;
- and c. hydrogenating the estrapentaene in the presence of a hydrogenation catalyst to said 1,3-oxygenated-8.alpha.-estratriene.
1 more element
Dependencies are inferred from the claim text.