2,6-Lutidine → HCID 67110015, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence