Sodium t-butoxide → HCID 51357134, compound

(R)-2-(2-(benzylamino)propoxy)acetyl chloride was dissolved in tert-butanol (500 mL). Sodium tert-butoxide (14.0 g, 125 mmol) was then added in one portion and the reaction mixture heated at reflux for 18 h. The reaction was cooled and concentrated under reduced pressure to remove the solvent. The residue was dissolved in diethyl ether (300 mL) and then washed with 2 N HCl (150 mL), H2O (150 mL) and saturated brine (100 mL). The organic phase was then dried (Na2SO4), filtered, and concentrated under reduced pressure to afford a light yellow oil. Purification by column chromatography (silica gel, 10-50% EtOAc in heptanes) afforded (R)-4-benzyl-5-methylmorpholine-3-one (17.2 g, 63%) as a light yellow oil. 1H NMR and MS consistent.

1. temperaturethe reaction mixture heated
2. temperatureat reflux for 18 h
3. temperatureThe reaction was cooled
4. concentrationconcentrated under reduced pressure
5. customto remove the solvent
6. dissolutionThe residue was dissolved in diethyl ether (300 mL)
7. washwashed with 2 N HCl (150 mL), H2O (150 mL) and saturated brine (100 mL)
8. dry with materialThe organic phase was then dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto afford a light yellow oil
12. customPurification by column chromatography (silica gel, 10-50% EtOAc in heptanes)

ORD record

ord-c4be7d0f93b74d91b2233e83f0e81282

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863271B2