1,1'-Carbonyldiimidazole → HCID 86673444, compound

Participants

Reaction Conditions

Reaction Steps

Optically-enriched tert-butyl (1R,2R)-1-(6-bromo-3-fluoropyridin-2-yl)-2-hydroxy-2-phenylethylcarbamate (208 mg, 0.506 mmol) was dissolved in trifluoroacetic acid (25% in dichloromethane, 10 mL). After 2 h at room temperature, the reaction was concentrated. The resulting residue was loaded onto a strong cation exchange cartridge which was flushed with several volumes of methanol and discarded. The product was eluted with 2M ammonia in methanol and concentrated. The resulting residue was suspended in tetrahydrofuran (2 mL), cooled to 0° C., and treated with carbonyldiimidazole (123 mg, 0.759 mmol). After 5 min, the ice bath was removed and stirring continued overnight. The reaction was quenched by addition of 2M ammonia in methanol and concentrated. The resulting residue was purified by column chromatography (25%→50% EtOAc/Hex) to give 96 mg (28%) as a white foam solid. Mass spec.: 337.0 (MH)+.

Provenance & Evidence