1-Methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole → 3-(5-Hydroxy-5-phenylpentanoyl)-4-phenyl-1,3-oxazolidin-2-one

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Reaction Steps

Under argon and at a temperature between 0° and −5° C., 5 g of 1-(2-oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione in 20 ml of dichloromethane are slowly, over a period of about 3 hours, added to a solution of 1.5 ml of boron-dimethylsulfide-complex in 25 ml of dichloromethane. The mixture is stirred at the same temperature for another 2 hours, the reaction being monitored by thin-layer chromatography. After the reaction has ended, 2 ml of methanol and 1.5 ml of 35 percent strength hydrogen peroxide solution and 1.1 ml of 3N sulfuric acid are added at below 0° C., and the mixture is stirred at room temperature for another 15 min. After phase separation, the organic phase is washed successively with 2N sulfuric acid, 5% strength sodium bisulfite solution and 10 percent strength sodium chloride solution and then dried and concentrated. After chromatography (SiO2, ethyl acetate/n-heptane=1:1, the product of molecular weight 339.4 (C20H21NO4); MS (DCl+): 322 (M+H+−H2O); (ESI+):403 (M+Na++CH3CN), 362 (M+Na+) is obtained. By adding optically active 1-methyl-3,3-diphenyltetrahydropyrrolo[1,2-c][1,3,2]oxazaborole (S or R, 0.75 ml) at from 0° to −5° C. to the reaction mixture prior to the addition of 1-(2-oxo-4-phenyloxazolidin-3-yl)-5-phenylpentane-1,5-dione, by the same route, 3 is obtained in diastereomerically enriched form.

Provenance & Evidence