HCID 14143058, compound → (S)-4-Benzyl-3-methylmorpholine

Temperature

60 °C

To a 0° C. solution of (5S)-5-methyl-4-(phenylmethyl)-3-morpholinone (12.74 g, 62.07 mmol) in toluene (150 mL) was added Red-Al (65% w/w in PhMe, 38 mL) dropwise via addition funnel. The resulting solution was heated at 60° C. and stirred for 4 h, then cooled to 40° C. and stirred overnight. The solution was then cooled to 0° C. and quenched by dropwise addition of 1 N aq. NaOH (15 mL). The mixture was diluted with Et2O (100 mL) and washed with 1 N aq. NaOH (100 mL) followed by brine (50 mL). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and azeotroped with MeOH (50 mL) to provide (3S)-3-methyl-4-(phenylmethyl)morpholine (11.33 g, 95%) as a faintly pink oil. LCMS: (M+H)+: 192.2.

1. additiondropwise via addition funnel
2. temperaturecooled to 40° C.
3. stirringstirred overnight
4. temperatureThe solution was then cooled to 0° C.
5. customquenched by dropwise addition of 1 N aq. NaOH (15 mL)
6. additionThe mixture was diluted with Et2O (100 mL)
7. washwashed with 1 N aq. NaOH (100 mL)
8. dry with materialThe organic phase was dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customazeotroped with MeOH (50 mL)

ORD record

ord-cdb24685340742d3afd59474bc35351f

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893056B2