PRODUCTION OF OPTICALLY ACTIVE PYRROLIDINE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a safe and simple method for producing the subject compound useful as a synthetic intermediate compound of a medicine such as an antibacterial agent by asymmetrically hydrogenating a specific pyrrolidinone by using a catalyst of a specific complex material. SOLUTION:...

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Bibliographic Details
Main Authors KIYOFUJI NOBUO, SOTOGUCHI TSUKASA, YUASA YOSHIFUMI
Format Patent
LanguageEnglish
Published 04.08.1998
Edition6
Subjects
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
THEIR RELEVANT APPARATUS
TRANSPORTING
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Summary:PROBLEM TO BE SOLVED: To provide a safe and simple method for producing the subject compound useful as a synthetic intermediate compound of a medicine such as an antibacterial agent by asymmetrically hydrogenating a specific pyrrolidinone by using a catalyst of a specific complex material. SOLUTION: This method for producing an optically active pyrrolidine derivative is constituted by asymmetrically hydrogenating 3-acetyl-1-benzyl-2- pyrrolidinone expressed by formula I by using a complex compound formed by a bi-dentate phosphine with ruthenium as a catalyst to form (3S, 1'R)-1- benzyl-3-[(1'-hydroxy)ethyl]-2-pyrrolidinone of formula II, reducing the obtained pyrrolidinone of the formula II, then mesylating or tosylating to form (3R, 1'R)-1-benzyl-3-[(1'-methanesulfonyloxy)ethyl]pyrrolidine of formula III, etc., and then performing the methylamination reaction of the pyrrolidine of formula II to obtain (3R, 1'S)-1-benzyl-3-[(1'-N-methylamino)ethyl]pyrrolidine expressed by formula IV.
Bibliography:Application Number: JP19970024514