http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1502409-A

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http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C405-00
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filingDate 1975-06-18-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1978-03-01-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1502409-A
titleOfInvention Prostaglandin intermediates
abstract 1502409 Cyclopentanone derivatives AMERICAN HOME PRODUCTS CORP 18 June 1975 [19 June 1974] 10112/77 Divided out of 1502328 Headings C2C and C2P The invention comprises cyclopentanones of the formulĀµ in which R<SP>1</SP> and R<SP>3</SP> each are C 1-3 alkyl; R<SP>2</SP> is H or a hydroxy protecting group, R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> each are H or C 1-3 alkyl and n is 2 to 5; with the proviso at least one of R<SP>4</SP>, R<SP>5</SP> or R<SP>6</SP> is H and the further proviso in compounds of Formula 4 above that R<SP>2</SP> is H when R<SP>6</SP> is C 1-3 alkyl and their preparation by condensing dialkyl cyclopropane-1,1-dicarboxylates of the Formula I wherein R<SP>1</SP> is C 1-3 alkyl with compounds of the formula wherein R<SP>3</SP> is C 1-3 alkyl, if desired, where R<SP>2</SP> in the resulting compounds of Formula III above is a hydroxy protecting group, removing said group, and treating the resulting compounds of Formula 3 in which R<SP>2</SP> is H with bases, and, if desired, for converting the compounds thus obtained in which R<SP>2</SP> and R<SP>6</SP> are both H into the corresponding compounds of Formula III in which R<SP>2</SP> is a hydroxy protecting group and R<SP>6</SP> is H. Dimethyl and dipropyl 2-formylcyclopropane- 1,1-dicarboxylate are obtained by reacting dimethyl bromomalonate with methanol and dipropyl bromomalonate with propanol respectively. Dialkyl cyclopropane - 1,1 - dicarboxylates of the Formula 1 above are prepared reacting the corresponding cyclopropane derivatives of the Formula XV resulting from the reaction between the appropriate dialkyl 2-formylcyclopropane-1,1-dicarboxylates and phosphonates of the formula wherein Alk is C 1-3 alkyl, with sodium borohydride or the appropriate C 1-3 alkylmagnesium halide, and, if desired, protecting the hydroxy groups of the resulting compounds. Phosphonates of the formula are prepared by dialkyl methylphosphonates with the appropriate esters of the formula in the presence of butyllithium.
priorityDate 1974-06-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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