反应详情

温度

80 °C

A mixture of 3.5 g of 2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl ]-phenyl]-3H-1,2,4-triazol-3-one, 0.6 g of a sodium hydride dispersion 50% and 100 ml of N,N-dimethylformarnide was stirred for 3 hours at 80° C. After the addition of 3.5 g of (R)-2-butanol 4-bromobenzenesulfonate (ester) (intermediate (3)), stirring was continued for 6 hours at this temperature. After cooling, water was added The crystallized product was filtered off and taken up in trichloromethane. The undissolved part was filtered off. The remaining solution was dried and purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4methyl-2-pentanone. The product was filtered off and converted into the (S)-7,7dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonate salt in 2-propanone. The salt was filtered off and recrystallized from 1-butanol. The product was filtered off and dried, yielding 1.2 g (13.7%) of (+)-(S)-2,4-dihydro-4-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one (S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonate (1:2); mp. 192.0° C.; [α]D20=+28.410° (conc.=1% in ethanol) (interm. 5).

1. stirringstirring
2. waitwas continued for 6 hours at this temperature
3. temperatureAfter cooling
4. filtrationwas filtered off
5. filtrationThe undissolved part was filtered off
6. customThe remaining solution was dried
7. custompurified by column chromatography over silica gel
8. customThe pure fractions were collected
9. customthe eluent was evaporated
10. customThe residue was crystallized from 4methyl-2-pentanone
11. filtrationThe product was filtered off
12. filtrationThe salt was filtered off
13. customrecrystallized from 1-butanol
14. filtrationThe product was filtered off
15. customdried