Process for the preparation of (+)-(1R) -cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid
AssigneeFirmenich SA
InventorsValentin Rautenstrauch, Jean-Jacques Riedhauser
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AssigneeFirmenich SA
InventorsValentin Rautenstrauch, Jean-Jacques Riedhauser
Estimating the term…
A method for preparing 3-oxo-2-pentyl-1-cyclopentaneacetic acid or methyl 3-oxo-2-pentyl-1-cyclopentaneacetate, essentially in the form of the (+)-(1R)-cis isomer thereof. The method includes the steps of (a) catalytically hydrogenating a compound of the formula (I), ##STR1## wherein M is a hydrogen atom, an alkali metal or alkaline earth metal atom, or a group NR.sub.4, where R is a hydrogen or a lower alkyl radical, in a suitable solvent and in the presence of a catalyst consisting of an Ru(II) complex comprising chiral ligands that contain a 2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl (BINAP) radical or a 1,2-bis(2,5-dialkylphospholano)benzyl (DuPHOS) radical, wherein the alkyl is a C.sub.2 or C.sub.3 radical, to give a compound of formula (II), ##STR2## wherein M has the meaning given above, essentially in the form of the (+)-(1R)-cis isomer thereof; (b) if required, acidifying, in a per se known manner, the compound of formula (II), wherein M is an alkali metal or alkaline earth metal atom, or a group N.sub.4, where R is hydrogen or a lower alkyl radical, to give (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid; and (c) if required, esterifying the resulting (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid under suitable conditions to form methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate.
Process for the preparation of 3-oxo-2-pentyl-1-cyclopentaneacetic acid, or of methyl 3-oxo-2-pentyl-1-cyclopentaneacetate, essentially in the form of their (+)-(1R)-cis configuration isomer, characterized in that it comprises the following steps:
Process for the preparation of (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid or of methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate, having a purity of at least 95%, characterized in that (+)-(1R,25,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid is oxidized by means of pyridinium chlorochromate, in the presence of sodium acetate, and, if necessary, the thus formed (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid is esterified under appropriate conditions.
Compound of formula ##STR13## wherein symbol M represents an atom of an alkaline or alkaline-earth metal, or a NR.sub.4 group, R representing hydrogen or a lower alkyl radical.
Compound selected from the group consisting of:
Dependencies are inferred from the claim text.