2,6-Lutidine → HCID 67110015, compound

Temperature

0 °C

To a round bottom flask charged with (+/−)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)morpholine-4-carboxylate (3.04 g, 9.17 mmol) in dichloromethane (45.8 ml) and cooled to 0° C. was added 2,6-lutidine (2.136 ml, 18.34 mmol). Trimethylsilyl trifluoromethanesulfonate (3.31 ml, 18.34 mmol) was added drop wise over 5 min. The reaction was slowly warmed to room temperature over 4 h. The reaction mixture was quenched by the addition of saturated aqueous sodium bicarbonate and dichloromethane. The mixture was transferred to a separatory funnel and the aqueous layer was extracted with dichloromethane (3×). The combined organics were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography on the ISCO system (0-10% MeOH/CH2Cl2). (+/−)-2-(((tert-Butyldimethylsilyl)oxy)methyl)morpholine (1.692 g) was isolated as a clear oil.

1. temperatureThe reaction was slowly warmed to room temperature over 4 h
2. customThe reaction mixture was quenched by the addition of saturated aqueous sodium bicarbonate and dichloromethane
3. customThe mixture was transferred to a separatory funnel
4. extractionthe aqueous layer was extracted with dichloromethane (3×)
5. washThe combined organics were washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified by column chromatography on the ISCO system (0-10% MeOH/CH2Cl2)

ORD record

ord-76843636a08949ee86c562d1b6b67770

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273057B2