2-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)- → (+)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone (S)-2-oxo-10-bornanesulfonate

Participants

Reaction Steps

10 G. of racemic 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone are maintained at reflux with stirring together with 11.3 g. of (+)-camphor-10-sulfonic acid monohydrate [α546 = +28.0° (water; c = 10%)] and 130 ml. of methyl ethyl ketone and the mixture is preferably seeded with a small amount of (+)-3-[2-{4-[(S)-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone-(S)-2-oxo-10-bornanesulfonate (1:2). An additional 70 ml. of methyl ethyl ketone are added after 3 hours. The mixture is maintained at reflux with stirring for 20 hours. The precipitate obtained is removed by filtration, washed with methyl ethyl ketone and dried under reduced pressure, and there is obtained white (+)-3-{2-[4-(8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}- 2-oxazolidinone-(S)-2-oxo-10-bornanesulfonate (1:2); αD = +14.1°; α365 = +102° (chloroform; c = 3.0%); melting point 164°-166° C.

Provenance & Evidence