3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 15382944, compound

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Reaction Steps

To a solution of (R)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 182, 10.18 g, 44.40 mmol) in THF (188 mL) at −78° C. was added methyl magnesium bromide (16.28 mL, 48.84 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight under nitrogen atmosphere. Re-cooled reaction mixture to −78° C. and added dropwise additional 13 mL (0.9 eq, to bring total to 2 eq) of methyl magnesium bromide. Allowed reaction mixture to stir at −78° C. for 3 hours and warm to room temperature. The reaction mixture was quenched with water and diluted with ethyl acetate saturated sodium chloride (brine). The resulting emulsion was filtered thru celite and the layers separated. The organic layers were dried over magnesium sulfate, filtered, concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a colorless oily solid (8.42 g, 77%).

Provenance & Evidence