Sodium hydride → HCID 88190938, compound

HRID 2306228Notes

Reaction equation

HRID 2306228 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][C:19]=1[CH2:29]Br>C1COCC1>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][C:19]=1[CH2:29][N:11]1[CH2:12][CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4198849tert-Butyl (2-oxopyrrolidin-3-yl)carbamateHCID 18536041HCID 18536041, compound

Product 1

HCID 88190938HCID 88190938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

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.

Workup

  1. additionwas added dropwise
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. customThe reaction was quenched with saturated aqueous NH4Cl (3 mL)
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between saturated aqueous NaHCO3 and EtOAc
  7. customThe layers were separated
  8. extractionthe organic extract
  9. washwas washed with H2O
  10. dry with materialbrine, then dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by silica gel chromatography
  14. washeluting with CH2Cl2—5% MeOH

Sources & evidence

ORD record
ord-76daadc1325f4d209f66b53ae5ef40f8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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