Water → HCID 20279337, compound

HRID 1248329Notes

Reaction equation

HRID 1248329 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2([CH2:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])[C:9]1=[O:23].[C:28]([O:34][CH2:35]Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2([CH2:20][C:19](=[O:21])[N:18]([CH2:35][O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:17]2=[O:22])[C:9]1=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 13691150HCID 13691150, compound

Product 1

HCID 20279337HCID 20279337, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.192 g., 50% w/w oil dispersion) was added to a stirred solution of 1'-(3,4-dichlorobenzyl)-spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (1.5 g.) in dry N,N-dimethylformamide (DMF) (20 ml.) under a nitrogen atmosphere. The solution was stirred for 30 minutes and then chloromethyl pivaloate (0.60 g.) was added. The mixture was stirred for 20 hours and then poured into water (30 ml.) The mixture obtained was extracted with ethyl acetate (2×40 ml.). The combined extracts were washed with water (2×15 ml.) dried (MgSO4) and evaporated. The residue was dissolved in ethyl acetate (20 ml.). Chromatographic silica gel (10 g.) was added to the solution and then the solvent was evaporated. The residue was added to a column of silica gel (400 g.) made up in ethyl acetate/petrol (60-80 (1:1 v/v). This solvent mixture was used to elute the column. Evaporation of those combined fractions of eluate containing the major component [relative flow value 0.6, as judged by TLC (SiO2 : 50% v/v EtOAc/toluene)] gave 1'-(3,4-dichlorobenzyl)-1-pivaloyloxymethyl-spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione as an oil which solidified slowly to give a solid (0.55 g.), m.p. 134°-135° C. (cyclohexane).

Workup

  1. stirringThe mixture was stirred for 20 hours
  2. customobtained
  3. extractionwas extracted with ethyl acetate (2×40 ml.)
  4. washThe combined extracts were washed with water (2×15 ml.)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in ethyl acetate (20 ml.)
  8. additionChromatographic silica gel (10 g.) was added to the solution
  9. customthe solvent was evaporated
  10. additionThe residue was added to a column of silica gel (400 g.)
  11. washto elute the column
  12. customEvaporation of those combined fractions of eluate
  13. additioncontaining the major component [relative flow value 0.6, as judged by TLC (SiO2 : 50% v/v EtOAc/toluene)]

Sources & evidence

ORD record
ord-f7a65354c0364965bbbf059c81622641
Source dataset
uspto-grants-1985_06
Patent number
US04523021

Reaction notes

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