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US 6,294,679 B1Granted
Intermediate for the synthesis of prostaglandins
AssigneeChirotech Technology Limited
InventorsPhilip Mark Jackson, Ian Campbell Lennon
Life of this patent
Estimating the term…
Abstract
An enantiomerically enriched compound of formula 1, wherein Ar is phenyl optionally substituted with one or more groups selected from haloalkyl, alkyl and halide. This compound can be isolated in crystalline form, and used in the preparation of (+)-16 [3-trifluoromethyl)phenoxy]-17,18,19,20-tetranor PGF2α isopropyl ester.
Claims5
An enantiomerically enriched compound of formula 1
- wherein Ar is phenyl optionally substituted with one or more groups selected from haloalkyl, alkyl and halide, wherein said isomer shown as formula 1 is more than 95% enantiomeric excess.
A compound which is 8-anti{4-[3-(trifluoro-methyl)phenoxy]-3R-dimethyl -tert-butylsilyloxy-1E-butenyl}-6-endo-dimethyl-tert -butylsilyloxy-2-oxabicyclo[3.2.1]octan-3-one.
A process for preparing a compound of formula 1
- wherein said process comprises the following steps:
- reaction of (−)-2-exo-bromo-3-endo-tert-butyldimethyl -silyloxybicyclo[3.2.0]heptan-6-one with base to form 3-endo-tert-butyldimethyl-silyloxytricyclo[3.2.02,7]heptanone;
- reaction of the latter compound with a cuprate reagent derived from (R)-4-(aryloxy)-3-(tert-butyldimethylsilyloxy)-1-iodo-1 E-butene or the corresponding alkyne;
- and Baeyer-Villiger oxidation of the resultant bicyclic ketone, with removal of the regioisomeric lactone via hydrolysis.
1 more element
Dependencies are inferred from the claim text.