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filingDate 1970-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1973-02-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1308182-A
titleOfInvention Process for the manufacture of cyclobutanones
abstract 1308182 Cyclobutanones; steroids SCHERING AG 6 March 1970 [6 March 1969 18 July 1969] 10860/70 Headings C2C and C2U The preparation of an isomeric mixture of a cyclobutan-2<SP>1</SP>-one and a cyclobutan-3<SP>1</SP>-one of the formula (wherein R 1 and R 2 are each alkyl or cycloalkyl, or R 1 and R 2 together with the adjacent carbon atom represent a cycloalkyl or steroid group, and one of T and U is O and the other is H 2 ) is effected by reacting a tertiary α-ketone of the formula (wherein X is Cl or Br) with dimethylmethylene sulphonium oxide. The mixture may be separated into the individual components by standard methods such as chromatography. Novel steroid products have the formula wherein C 5 = C 6 is a single or double bond, V is H or CH 3 , and the A ring is one of the structures in which W is H, alkyl, tetrahydropyranyl or acyl, Z is H or CH 3 and Y is H 2 , H(OH), H(OR) or ethylenedioxy, R being alkyl or acyl. In these products an esterified OH group may be hydrolysed and a free OH group esterified. In the preparation of the cyclobutanones the reagent may be liberated from a trimethyl sulphoxonium salt in an aprotic solvent with an anhydrous base. Reactive keto groups in steroid starting materials must be protected, e.g. by ketalization. Named non-steroid products are 3,3 - dimethyl - cyclobutan - 1 - one, 2,2 - dimethyl - cyclobutan - 1 - one and spiro[3,5]nonan-2-one. The novel steroids are pharmacologically active, e.g. they show a strong testicle and prostate inhibition in male rats and inhibit ovulation in female rats, and they may be made up into pharmaceutical compositions with suitable carriers.
priorityDate 1969-03-06-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 32.