2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 117698840, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-methoxycarbonylmethyl-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound AI) (130 mg, 0.39 mmol) in anhydrous THF at −78° C. was added 1 M NaN(trimethylsilyl)2 in THF (0.43 mL, 0.43 mmol) during a period of 5 mins. Then the mixture was stirred for 20 mins at −78° C. To this solution was added a pre-cooled (−78° C.) solution of 2-(phenylsulfonyl)-3-phenyloxaziridine (153 mg, 0.585 mmol) in THF. The solution was stirred for 30 mins at −78° C. and then quenched by rapid addition of 6N HCl. The mixture was stirred at room temperature for 30 mins and then diluted with dichloromethane. The mixture was washed with water and 5% aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography to afford 7-(hydroxy-methoxycarbonyl-methyl)-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound AJ) (0.30 g, 85%). MS: calc'd (MH+) 350, measured (MH+) 350.

Provenance & Evidence