Hydrogen Peroxide → HCID 6355768, compound

Participants

Reaction Steps

A solution of (R)-4-benzyl-3-((1R,2R,4R)-2,4-dimethylcyclohexanecarbonyl) oxazolidin-2-one (0.65 g, 2.0 mmol) in THF/water (3:1, 20 mL) was cooled in an ice bath and 30% H2O2 (1 mL, 16.5 mmol) was slowly added, followed by LiOH*H2O(s) (0.17 g, 4.0 mmol) in one portion. The reaction was allowed to slowly warm to room temperature and stirred for 16 h. The reaction was then cooled in an ice bath. A 1 M solution of Na2SO3 was very slowly added to the cooled reaction mixture. The solution was stirred for 1 h, and the layers were separated. The organics were removed under reduced pressure. The aqueous was added back to the organics concentrate and was washed with CH2Cl2 (2×50 mL). The pH of the aqueous solution was adjusted to 2 through slow addition of concentrated hydrochloric acid. The resulting mixture was extracted with EtOAc (1×50 mL) and dried over Na2SO4. Solvents were removed under reduced pressure, co-evaporating with hexanes, to afford 0.300 g of (1R,2R,4R)-2,4-dimethylcyclohexanecarboxylic acid as a white solid.

Provenance & Evidence