One pot synthesis of 2-oxazolidinone derivatives

Details One pot synthesis of 2-oxazolidinone derivatives One pot synthesis of 2-oxazolidinone derivatives

2000-02-02

2000-12-12

Lambkin, Deborah C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26304

Patent

active

061601233

ABSTRACT:
The present invention provides an improved process for preparing (S)-4-{[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone which comprises: a) forming a carbamate of formula (III), from methyl 4-nitro-(L)-phenylalaninate hydrochloride; b) reducing the compound of formula (III) to give the compound of formula (IV); c) reducing the methyl ester grouping in the compound of formula (IV) to give the compound of formula (V); d) ring closure of the compound of formula (V) to give the compound of formula (VI); e) diazonium salt formation from the compound of formula (VI) followed by reduction to give the compound of formula (VII); f) Fischer reaction of the compound of formula (VIl) to give (S)-4-{[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone.

REFERENCES:
patent: 5399574 (1995-03-01), Robertson et al.
patent: 5466699 (1995-11-01), Robertson et al.
patent: 5863935 (1999-01-01), Robertson et al.
International Search Report for PCT/GB/01885, Sep. 1996.

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