Benzyl Bromide → HCID 18449405, compound

HRID 656368Notes

Reaction equation

HRID 656368 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:23](=[O:24])[C:11]3([CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=4)[CH2:12]3)[NH:10][C:9]2=[O:25])=[CH:5][CH:4]=1.[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[CH2:30]([N:10]1[C:11]2([CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=3)[CH2:12]2)[C:23](=[O:24])[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=2)[C:9]1=[O:25])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18449403HCID 18449403, compound

Product 1

HCID 18449405HCID 18449405, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-1-(4-methoxybenzyl)-5′-nitro-spiro[imidazolidine-4,2′-indane]-2,5-dione from Step A (165 mg, 0.45 mmol) in DMF (1 mL) was added sodium hydride (18 mg of a 60% dispersion in mineral oil, 0.45 mmol). The mixture was stirred for 5 min at ambient temperature and benzyl bromide (230 mg, 1.35 mmol) was added. After 30 min, the mixture was partitioned between saturated aqueous NaHCO3 (3 mL) and CHCl3 (5 mL). The aqueous phase was extracted further with CHCl3 (5 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with hexane:EtOAc—75:25, to give the title compound. MS: m/z=458 (M+1).

Workup

  1. waitAfter 30 min
  2. customthe mixture was partitioned between saturated aqueous NaHCO3 (3 mL) and CHCl3 (5 mL)
  3. extractionThe aqueous phase was extracted further with CHCl3 (5 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexane

Sources & evidence

ORD record
ord-097aaaba56cd4b429aef364a2a528f5f
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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