Process for preparing optically active 4-hydroxy-2-pyrrolidone

Details Process for preparing optically active 4-hydroxy-2-pyrrolidone Process for preparing optically active 4-hydroxy-2-pyrrolidone

1997-01-29

1998-11-17

Ambrose, Michael G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D207273

Patent

active

058378774

ABSTRACT:
A process for preparing optically active 4-hydroxy-2-pyrrolidone comprising asymmetrically hydrogenating an N-substituted-4-amino-3-oxobutanoic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a benzyloxycarbonyl group, the benzene ring of which may be substituted; and R.sup.2 represents a lower alkyl group having 1 to 4 carbon atoms, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active N-substituted-4-amino-3-hydroxybutanoic ester, deblocking, and cyclizing the ester. A series of the reactions can be carried out in one pot. Optically active 4-hydroxy-2-pyrrolidone is obtained in high yield with high optical purity, and is useful in the synthesis of carbapenem antibiotics

REFERENCES:
patent: 4250093 (1981-02-01), Pesa et al.
patent: 5276164 (1994-01-01), Laffan et al.

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