Ozone → HCID 58055033, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-methoxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate (230 mg) in CH2Cl2 (10 mL) was cooled to −78° C. and treated with a stream of ozone until a blue color persisted. A stream of nitrogen was passed through the solution for 15 minutes to remove excess ozone from solution. The solution was then treated with dimethylsulfide (0.2 mL) and allowed to warm to 23° C. over 30 min. Volatile components of the reaction mixture were removed in vacuo. The residue was dissolved in methanol (10 mL). To the solution was added NaBH4 (50 mg) at 0° C. and the mixture was stirred at 0° C. for 30 minutes. The mixture was poured into saturated aqueous solution of NH4Cl and extracted with CHCl3. The extract was washed with brine, dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=99/1˜1/99) to give tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-(2-hydroxyethyl)-3-methoxypyrrolidine-1-carboxylate as a pale yellow foam.

Provenance & Evidence