L-Tartaric acid → 3-[2-{4-[(R)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone (R,R)-tartrate

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Reaction Steps

5.0 G. of the salt of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone with (+)-(R,R)-tartaric acid [α546 =+15.0° (water; c = 10%)] in the molar ratio of 1:1 are dissolved in 500 ml. of acetone and, after stirring for 24 hours at room temperature, the mixture is filtered. The filter cake is washed with acetone, dried under reduced pressure, and there is obtained 3-[2-{4-[(R)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone-(R,R)-tartrate (1:1); α365 =+98.6° (dimethylformamide; c = 2.0%); decomposition point 172° C. After liberation of the base by treatment with aqueous sodium hydroxide, there is obtained crystalline (R)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone; α365 =+183.85° (chloroform; c = 0.5%) in a purity above 99%. The yield amounts to 54.4% of theory.

Provenance & Evidence