PRODUCTION OF ENANTIOMER PURE DIESTER OF 3-HYROXYOCTANEDIOIC ACID, DIESTER OF (R)-3-HYDROXYOCTANEDIOIC ACID AND PRODUCTION OF (R)-(+)-AND (S)-(-)-ALFA-LIPOIC ACID

PRODUCTION OF ENANTIOMER PURE DIESTER OF 3-HYROXYOCTANEDIOIC ACID, DIESTER OF (R)-3-HYDROXYOCTANEDIOIC ACID AND PRODUCTION OF (R)-(+)-AND (S)-(-)-ALFA-LIPOIC ACID

PROBLEM TO BE SOLVED: To produce both enantiomer of α-lipoic acid in high chemical and optical yield by using a cheap starting material and carrying out asymmetric hydrogenation of a ketone. SOLUTION: An asymmetric, chemical and catalytic hydrogenation of 3-oxo- octanedioic acid diester of formula I...

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Hauptverfasser: GEWALD RAINER DR, LABAN GUNTER DR
Format: Patent
Sprache:eng
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ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
PERFORMING OPERATIONS
PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Zusammenfassung:PROBLEM TO BE SOLVED: To produce both enantiomer of α-lipoic acid in high chemical and optical yield by using a cheap starting material and carrying out asymmetric hydrogenation of a ketone. SOLUTION: An asymmetric, chemical and catalytic hydrogenation of 3-oxo- octanedioic acid diester of formula I (R and R are each a 1-20C alkyl, a 3-12C cycloalkyl a 7-12C aralkyl or an aryl) is carried out in the presence of a complex comprising ruthenium and an optically active phosphine, or a Raney nickel and an optically active tartaric acid to provided enantiomerically pure 3- hydroxyoctanedioic acid diester of formulas II and III. The asymmetric hydrogenation is carried out at 20-140C under 1-100 bar pressure.