(-)-Pseudoephedrine → (4R,5R)-2-(2-Bromo-4-fluoro-phenyl)-3,4-dimethyl-5-phenyl-oxazolidine

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Reaction Steps

To a solution 2-bromo-4-fluorobenzaldehyde (15.2 g, 74.9 mmol) in toluene (80 ml) was added (1R,2R)-(−)-pseudoephedrine (13.6 g, 82 mmol) and the resulting mixture was refluxed removing water using a Dean-Stark trap for 16 h. The reaction was halted and cooled down to room temperature. The solution was washed with citric acid solution (1M, 100 ml), saturated sodium bicarbonate solution (50 ml), brine (50 ml) and dried (MgSO4). Then, it was filtered and the solvent was evaporated under vacuum to give title compound as yellow oil. (26.2, yield=97%).

Provenance & Evidence