Hydrogen Peroxide → HCID 22882479, compound

Participants

Reaction Steps

2.5 ml of diborane-dimethylsulfide complex are added to 18.0 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[(1-vinylcyclopropyl)methyl]-1,3-oxazolidine, dissolved in 300 ml of tetrahydrofuran at 0° C. in the course of 3 minutes and the mixture is then stirred for 3 h, while cooling with ice. 5 ml of water, 16 ml of 2N sodium hydroxide solution and 8.5 ml of a 30% hydrogen peroxide solution are added in succession and the mixture is subsequently stirred at room temperature for 1 h. It is then diluted with ice-cold potassium carbonate solution and the aqueous phase is extracted with ethyl acetate. Purification of the crude product is carried out over 900 g of silica gel (mobile phase B): Rf (B)=0.25; anal. calc. for C16H35NO4 : C 64.18%, H 9.76%, N 4.68%; found C 64.05%, H 9.76%, N 4.73%.

Provenance & Evidence