PRODUCTION OF (R)-2-HYDROXY-4-PHENYL-3-BUTENOIC ACID

PRODUCTION OF (R)-2-HYDROXY-4-PHENYL-3-BUTENOIC ACID

PURPOSE:To obtain the subject compound by stereoselectively reducing 2-oxo-4- phenyl-3-butenoic acid readily available from benzaldehyde and pyruvic acid using a complex of L-proline with sodium borohydride. CONSTITUTION:2-Oxo-4-phenyl-3-butenoic acid readily available by reaction of benzaldehyde wi...

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser: IKEBE TSUGIO, KITAJIMA HIROSHI, MURAKAMI OSAMU
Format: Patent
Sprache:eng
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
COMPOUNDS THEREOF
INORGANIC CHEMISTRY
METALLURGY
NON-METALLIC ELEMENTS
ORGANIC CHEMISTRY
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Beschreibung
Zusammenfassung:PURPOSE:To obtain the subject compound by stereoselectively reducing 2-oxo-4- phenyl-3-butenoic acid readily available from benzaldehyde and pyruvic acid using a complex of L-proline with sodium borohydride. CONSTITUTION:2-Oxo-4-phenyl-3-butenoic acid readily available by reaction of benzaldehyde with pyruvic acid is subjected to reductive reaction using a complex of L-proline with sodium borohydride to stereoselectively provide (R)-2-hydroxy-4-phenyl-3-butenoic acid, which is then subjected to reductive reaction to stoichiometrically afford (R)-2-hydroxy-4-phenylbutanoic acid. The subject compound of high optical purity can readily and efficiently be produced according to the aforementioned method. The above-mentioned compound is useful as an industrial and extremely advantageous raw material for medicines.