反应详情

To a solution of 4-benzyl-6-(4-octyloxy-phenyl)-morpholin-3-one (22.22 g; 56.2 mmol) in THF (400 mL) was added borane-THF complex (1M, 140.4 mL; 140.4 mmol) dropwise, at 0° C. After 1 hour the mixture was allowed to warm to RT and stirred for another 2 hours. To the reaction mixture was added MeOH (30 mL), at 0° C., and the resulting mixture was stirred at RT for 30 minutes, and subsequently concentrated in vacuo. The residue was suspended in MeOH (300 mL.) and 1 M aqueous NaOH (112 mL) was added and heated under reflux for 1 hour. The resulting mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 5% aqueous NaHCO3-solution. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford 4-benzyl-2-(4-octyloxy-phenyl)-morpholine (20.33 g), which was used as such in the next step.

1. customat 0° C
2. stirringat 0° C., and the resulting mixture was stirred at RT for 30 minutes
3. concentrationsubsequently concentrated in vacuo
4. addition1 M aqueous NaOH (112 mL) was added
5. temperatureheated
6. temperatureunder reflux for 1 hour
7. concentrationThe resulting mixture was concentrated in vacuo
8. customthe residue was partitioned between EtOAc and 5% aqueous NaHCO3-solution
9. dry with materialThe organic layer was dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo