Hydrogen Peroxide → HCID 12788386、化合物

A solution of 7.98 g of 3-(2-fluorophenyl)-1-methyl-4-piperidone in 40 ml of dry tetrahydrofuran is cooled to 5° C. under nitrogen and treated dropwise with 49 ml of a 1.0 molar tetrahydrofuran solution of lithium tri-secondary butylborohydride, keeping the pot temperature below 10° C. The mixture is then stirred 18 hours at room temperatue under nitrogen. The mixture is cooled while 175 ml of 10% aqueous NaOH solution are added, keeping the pot temperature below 10° C. 117 ml of 30% H2O2 solution are added to the cooled mixture at a rate sufficient to keep the pot temperature at 30°-40° C. The mixture is stirred for 18 hours at ambient temperature followed by refluxing for one hour under nitrogen. The mixture is cooled and the phases are separated. The aqueous phase is extracted with dichloromethane and the combined organic phases are concentrated in vacuo. The residue is treated with 250 ml of cyclohexane and the mixture is concentrated. The residue is partitioned between dichloromethane and saturated NaCl solution. The dichloromethane phase is dried over anhydrous Na2SO4, filtered and concentrated in vacuo to a solid. This material is triturated with ether, filtered and dried to afford a solid. This material is recrystallized from benzene to afford cis-3-(2-fluorophenyl)-1-methyl-4-piperidinol, m.p. 158.5°-160° C.

1. customthe pot temperature below 10° C
2. additionare added
3. customthe pot temperature below 10° C
4. customat 30°-40° C
5. stirringThe mixture is stirred for 18 hours at ambient temperature
6. temperatureby refluxing for one hour under nitrogen
7. temperatureThe mixture is cooled
8. customthe phases are separated
9. extractionThe aqueous phase is extracted with dichloromethane
10. concentrationthe combined organic phases are concentrated in vacuo
11. additionThe residue is treated with 250 ml of cyclohexane
12. concentrationthe mixture is concentrated
13. customThe residue is partitioned between dichloromethane and saturated NaCl solution
14. dry with materialThe dichloromethane phase is dried over anhydrous Na2SO4
15. filtrationfiltered
16. concentrationconcentrated in vacuo to a solid
17. customThis material is triturated with ether
18. filtrationfiltered
19. customdried
20. customto afford a solid
21. customThis material is recrystallized from benzene

ORDレコード

ord-0f3c30f4637b438f863b27a5a20f7c24

出典データセット

uspto-grants-1983_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04382141