(+)-OR (-)-8-HALOGEN-6-HYDROXY-OCTANOIC ACID, ESTER AND SALT OF THE SAME, PRODUCTION OF THE SAME AS OPTICALLY PURE FORM AND PURE ALPHA-LIPOIC ACID AND DIHYDROLIPOIC ACID AS MIRROR IMAGE ISOMERS

Title:

(+)-OR (-)-8-HALOGEN-6-HYDROXY-OCTANOIC ACID, ESTER AND SALT OF THE SAME, PRODUCTION OF THE SAME AS OPTICALLY PURE FORM AND PURE ALPHA-LIPOIC ACID AND DIHYDROLIPOIC ACID AS MIRROR IMAGE ISOMERS

Document Type and Number:

Japanese Patent JPH09169692

Kind Code:

A

Abstract:

To obtain the subject new compound enabling to obtain an α-lipoic acid and a dihydrolipoic acid as mirror image isomers at an extremely high yield.

The (+)- or (-)-8-halogen-6-hydroxy-octanoic acid of formula I (X is Cl, Br or I) is obtained by decomposing a pure diastereomer salt of formula II by its reaction with an inorganic or organic acid or base. Further, an optically pure isomer of 8-halogen-6-hydroxy-octanoic acid alkyl ester of formula III (R is a linear or branched chain 1-4C alkyl) is obtained by stereoselectively converting the optically pure isomer of 6-hydroxy-octanoic acid of formula I, while maintaining the steric configuration in the presence of a catalytic amount of HCl, at 50-100°C in a corresponding alcohol as a solvent.

Inventors:

GEWALD RAINER DR (DE)
BEISWENGER THOMAS DR (DE)
LABAN GUNTER DR (DE)

Application Number:

JP24363896A

Publication Date:

June 30, 1997

Filing Date:

September 13, 1996

Export Citation:

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Assignee:

DRESDEN ARZNEIMITTEL (DE)

International Classes:

C07C51/41; C07C51/43; C07C51/487; C07C59/115; C07C67/08; C07C67/333; C07C69/675; C07D339/04; (IPC1-7): C07C59/115; C07C51/41; C07C51/43; C07C67/08; C07C69/675

Attorney, Agent or Firm:

Toshio Yano (3 outside)

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