Hydrogen Peroxide → HCID 24983448, compound

Participants

Reaction Steps

5.00 g (9.6 mmol) (3R,4S)-4-[4-(tert-butyl-dimethyl-silanyl-oxy)-phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxo-propyl]-azetidin-2-on was solved in 9.6 ml water-free dichloromethane, and then 1.92 ml (0.96 mmol) (R)-o-tolyl-CBS-oxazaborolidine 0.5 M-toluenic solution was added. The mixture was cooled to a temperature between 0 and −5° C., and at this temperature a dichloromethanic solution of 1.9 ml 1.0 M borane-dimethyl was added for 6 h. The reaction mixture had been stirred at this temperature until the spot of the starting keton disappeared according to the thin-layer chromatographic investigation. Then 10 ml methanol, 0.5 ml 5% hydrogen-peroxide solution, and 10 ml 2M sulphuric acid were added. Having been stirred the mixture for 0.5 h, the phases were separated. The organic phase was washed with 50 ml 2N sulphuric acid and then 50 ml 5% sulphite-solution. The solution was dried on anhydrous sodium-sulphate, filtered and evaporated.

Provenance & Evidence