Stereospecific enrichment of heterocyclic enantiomers
AssigneeR. T. Alamo Ventures I, LLC
InventorsStefan Kwiatkowski, Miroslaw Golinski, Joseph Kupper
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Abstract
The present invention describes methods for the stereoselective synthesis of heterocyclic enantiomers. The methods of the present invention incorporate the stereo-preferred oxidation of quinolone thiomethyl intermediates by optically active camphor based oxaziridines to provide R(+) or S(−) quinolone methylsulfinyl derivatives.
Claims6
A method of synthesizing 7-fluoro-1-methyl-3-methylthio-4-quinolone, comprising:
- a) providing:
- i) a racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone;
- ii) triphenylphosphine;
- and
- b) reacting, in a solvent, said racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone with said triphenylphosphine under conditions such that 7-fluoro-1-methyl-3-methylthio-4-quinolone is produced.
A method of synthesizing (S)-(−)-7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone in enantiomeric excess, comprising:
- a) providing:
- i) a racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone;
- ii) triphenylphosphine;
- b) reacting, in a solvent, said racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone with said triphenylphosphine under conditions such that 7-fluoro-1-methyl-3-methylthio-4-quinolone is produced;
- and
- c) treating said 7-fluoro-1-methyl-3-methylthio-4-quinolone with (1S)-(+)-(10-camphorsulfonyl)oxaziridine under conditions such that (S)-(−)-7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone is produced in enantiomeric excess.
A method of synthesizing (R)-(+)-7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone in enantiomeric excess, comprising:
- a) providing:
- i) a racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone;
- ii) triphenylphosphine;
- b) reacting, in a solvent, said racemic mixture of 7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone with said triphenylphosphine under conditions such that 7-fluoro-1-methyl-3-methylthio-4-quinolone is produced;
- and
- c) treating said 7-fluoro-1-methyl-3-methylthio-4-quinolone with (1R)-(−)-(10-camphorsulfonyl)oxaziridine under conditions such that (R)-(±)-7-fluoro-1-methyl-3-methylsulfinyl-4-quinolone is produced in enantiomeric excess.
Dependencies are inferred from the claim text.