1-Acetoxy-2-bromoethane → HCID 67490873, compound

Participants

Reaction Steps

(3S)-3-Hydroxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.0 g, 6.26 mmol) and bromoethyl acetate (2.09 g, 12.52 mmol) were dissolved in tetrahydrofuran (40 mL). Sodium hydride (0.33 g, 7.51 mmol) was added at 0° C., and the mixture was stirred at room temperature for 18 hours. A saturated ammonium chloride solution (100 mL) was added to the reaction solution at 0° C., followed by extraction with ethyl acetate (300 mL). The organic layer was washed with water (100 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (40% ethyl acetate/hexane) to give 1.74 g of the title compound as a colorless oil.

Provenance & Evidence