Sodium hydride → HCID 88190938, compound

Participants

Reaction Steps

To a solution of 3-(tert-butoxycarbonylamino)-2-oxopyrrolidine, as described above in Step A, (1.00 g, 4.99 mmol) in THF (10 mL) was added sodium hydride (230 mg of a 60% dispersion in oil, 5.75 mmol) in THF (5 mL), dropwise. The resulting mixture was stirred for 30 min at ambient temperature, then a solution of methanesulfonic acid 4-bromo-3-bromomethylphenyl ester, as described above in Step C, (1.96 g, 5.70 mmol) in THF (6 mL) was added dropwise and stirring was continued for 2 hours. The reaction was quenched with saturated aqueous NH4Cl (3 mL), then concentrated in vacuo. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The layers were separated and the organic extract was washed with H2O, then brine, then dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CH2Cl2—5% MeOH, to yield the titled product.

Provenance & Evidence