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US 5,155,251 AGranted
Process for the synthesis of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate
AssigneeWarner-Lambert Company
InventorsDonald E. Butler, Tung V. Le, Alan Millar, Thomas N. Nanninga
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Abstract
An improved process for the preparation of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate is described where a halo hydroxyester or other activated dihydroxyester is converted in two steps to the desired product.
Claims8
A process for the preparation of the compound of Formula I. ##STR9## which comprises:
- (a) treating a compound of Formula V ##STR10## wherein R is alkyl of from one to ten carbon atoms, allyl, or benzyl and X is a leaving group with a compound of Formula IV
- R.sup.1 --CN IV
- wherein R.sup.1 is a tetraalkylammonium, silver, copper (I), copper (II), an alkali metal or an alkaline earth metal in a solvent at about 0.degree.C. to about the reflux temperature of the solvent to afford a compound of Formula II ##STR11## wherein R is as defined above;
- or optionally treating a compound of Formula VI ##STR12## wherein R is as defined above with a compound of Formula IV in a solvent at about 0.degree. C. to about the reflux temperature of the solvent to afford a compound of Formula II;
- and
- (b) treating a compound of Formula II with a compound of Formula III ##STR13## wherein R.sup.2 is zinc, magnesium or lithium and a solvent at about -80.degree. C. to about room temperature to afford the compound of Formula I.
3 more elements
Dependencies are inferred from the claim text.