Hydrogen Peroxide → 2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid

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Reaction Steps

A solution of 2-cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-yl-butane-1,4-dione (1.63 g, 4.13 mmol) in THF (20 mL) was treated with lithium hydroxide monohydrate (0.226 g, 5.37 mmol) and hydrogen peroxide (2 mL of a 30% solution) and the mixture was stirred overnight at ambient temperature. The mixture was treated with sodium nitrite (1.3 g) and stirred for an additional 30 minutes. The organic solvent was removed under reduced pressure and the residual mixture was diluted with water (30 mL). The dilution was extracted with methylene chloride (3×30 mL) and the aqueous layer was acidified to pH 2 with 1M hydrochloric acid and extracted with dichloromethane (3×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to dryness to provide 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acid (0.56 g, 48%).

Provenance & Evidence