Benzyl Bromide → tert-butyl [1'-benzyl-5-chloro-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

HRID 883654Notes

Reaction equation

HRID 883654 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[NH:12][CH2:11]3)[C:9](=[O:16])[N:8]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:5]2=[CH:6][CH:7]=1.[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[CH2:27]([N:12]1[C:13](=[O:15])[CH2:14][C:10]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:8]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]2=[O:16])[CH2:11]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 24827314tert-butyl (5-chloro-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H) yl)acetate

Product 1

HCID 24827315tert-butyl [1'-benzyl-5-chloro-2,5'-dioxospiro[indole-3,3'-pyrrolidin]-1(2H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (5-chloro-2,5′-dioxospiro[indole-3,3′-pyrrolidin]-1(2H)-yl)acetate, intermediate 32 (175.00 mg; 0.50 mmol) in dry THF (5 mL), sodium hydride (24 mg; 0.60 mmol) was added. The reaction mixture was stirred 15 minutes then benzyl bromide (71.10 μl; 0.60 mmol) was added. After stirring for 10 min, the solvent was evaporated and the residue redissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and removed in vacuo to give a residue which was purified by chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate (20 to 50%) to give the title compound was obtained (220 g, 52.1%, HPLC purity 96.7%). MS (ESI+): 441.4; MS (ESI−): 439.2

Workup

  1. stirringAfter stirring for 10 min
  2. customthe solvent was evaporated
  3. dissolutionthe residue redissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customremoved in vacuo
  7. customto give a residue which
  8. customwas purified by chromatography (silica)
  9. washeluting with cyclohexane containing
  10. temperatureincreasing amounts of ethyl acetate (20 to 50%)

Sources & evidence

ORD record
ord-7d1c9024bcaf484cafbabb336a24fa78
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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