Hydrogen Peroxide → HCID 15290764, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [4R-[3(R*),4α,5α]]-3 [azido(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)acetyl]-4-methyl5-phenyl-2-oxazolidinone (13.7 g, 30.27 mmol) in 4:1 tetrahydrofuran water (300 mL) at 0° C., is added a solution of lithium hydroxide (2.5 g, 60.54 mmol) in hydrogen peroxide (17.2 mL, 151.35 mmol, 30% aqueous) dropwise under nitrogen. The milky mixture is stirred at 0° C. for 1 hour. Aqueous sodium sulfite (50 mL) is added. The bulk o the tetrahydrofuran is evaporated in vacuo. The aqueous solution is cooled in an ice bath and acidified with 6N hydrochloric acid to pH 1. The white solid is extracted with dichloromethane (5X) and dried (magnesium sulfate). Evaporation of solvent in vacuo gives a yellow oil, which is purified by flash chromatography (silica gel, hexane ethyl acetate acetic acid/100:50:1) to yield the title compound as a white solid, 8.3 g; mp 101°-102° C., [α]D =-38.7° (c=1.0, methanol). The chiral auxiliary ((4R)-methyl-(5S) phenyl-2-oxazolidinone) is recovered as a white solid, 5.2 g; mp 120°-122° C.

Provenance & Evidence