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Novel inversion process
| Details |
Inventors: Warnant, Julien; Marechal-Prost, Jacques; Cosquer, Philippe;
Assignee: Roussel UCLAF (Paris, FR)
Primary Examiner: Roberts; Elbert L.
Assistant Examiner: Eakin; Molly C.
Attorney, Agent or Firm: Hammond & Littell
A process for the preparation of an ester of chiral (A) acid with an optically active (S) .alpha.-cyano-3-phenoxybenzyl alcohol by reacting an ester of chiral (A) acid with .alpha.-cyano-3-phenoxybenzyl alcohol of the formula ##STR1## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions designated herein as "ester (R+S)" with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble. |
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DETAILED DESCRIPTION We claim: 1.
A process for the preparation of an ester of a chiral (A) acid and (S) .
alpha.
-cyano-3-phenoxybenzyl alcohol comprising reacting an ester of chiral (A) acid with .
alpha.
-cyano-3-phenoxybenzyl alcohol of the formula ##STR7## in its optically active (R) form or a racemic (R,S) mixture or a mixture of esters of said (R) alcohol and (S) alcohol in non-equimolecular proportions with a base selected from the group consisting of ammonium hydroxide, primary, secondary and tertiary amines, quaternary ammonium compounds, liquid amines of high molecular weight, ion exchange resins of a basic character and a catalytic amount of a strong base in at least one solvent in which the ester of the (R) alcohol is soluble and in which the ester of the (S) alcohol is insoluble and recovering from the resulting medium the chiral (A) acid ester of the (S) alcohol which is insoluble.
2.
The process of claim 1 wherein the basic agent is selected from the group consisting of ammonium hydroxide, secondary and tertiary amines and a catalytic amount of a strong base.
3.
The process of claim 2 wherein the chiral (A) acid is selected from the group consisting of an acid with one asymetric carbon atom and an acid with 2 asymetric carbon atoms.
4.
The process of claim 1 wherein the chiral (A) acid is selected from the group consisting of an acid with one asymetric carbon atom and an acid with 2 asymetric carbon atoms and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character.
5.
The process of claim 2 wherein the chiral (A) acid is a cyclopropane carboxylic acid with 2 asymetric carbon atoms in the ring.
6.
The process of claim 5 wherein the chiral (A) acid is a cis or trans optically active cyclopropane carboxylic acid of the formula ##STR8## wherein Hal is chlorine or bromine.
7.
The process of claim 1 wherein the chiral (A) acid is a cis or trans, optically active cyclopropane carboxylic acid of the formula ##STR9## wherein Hal is chlorine or bromine and the basic agent is selected from the group consisting of primary amines, quaternary ammonium compounds, high molecular weight liquid amines and ion exchange resins of a basic character
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