Potassium Carbonate → 2-(3-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)propyl)-2,3-dihydro-1 H-isoindole-1,3-dione

HRID 344232Notes

Reaction equation

HRID 344232 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][NH:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([CH2:22][CH2:23][CH2:24][N:25]2[C:29](=[O:30])[C:28]3[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:26]2=[O:35])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 4250767tert-butyl N-((pyrrolidin-3-yl)methyl)carbamate

Product 1

HCID 537857162-(3-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)propyl)-2,3-dihydro-1 H-isoindole-1,3-dioneYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (200 ml) was added to 3-(tert-butoxycarbonylaminomethyl)pyrrolidine (14 g), and potassium carbonate (30 g) and N-(3-bromopropyl)phthalimide (18 g) were added at room temperature with stirring, and the mixture was stirred at room temperature for 8 hr. The reaction mixture was concentrated under reduced pressure, and aqueous potassium carbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The mixture was dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography to give 17 g of 2-(3-(3-tert-butoxycarbonylaminomethylpyrrolidin-1-yl)propyl)-2,3-dihydro-1 H-isoindole-1,3-dione.

Workup

  1. additionwere added at room temperature
  2. stirringthe mixture was stirred at room temperature for 8 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and aqueous potassium carbonate solution
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe mixture was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e0ecd9dfd66b4de5aea771bac00e1ea6
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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