N-Hydroxyphthalimide → 2-(2-(2-Oxo-pyrrolidin-1-yl)-ethoxy)-isoindol-1,3-dione

HRID 661724Notes

Reaction equation

HRID 661724 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:9]=[C:5]1[CH2:6][CH2:7][CH2:8][N:4]1[CH2:3][CH2:2][O:1][N:30]1[C:34](=[O:35])[C:33]2[C:32](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]1=[O:40]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 231323402-(2-(2-Oxo-pyrrolidin-1-yl)-ethoxy)-isoindol-1,3-dioneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Hydroxy-ethyl)-pyrrolidin-2-one (1.00 g, 7.74 mmol, commercial product), PPh3 (2.07 g, 7.90 mmol), N-hydroxy-phthalimide (1.29 g, 7.90 mmol), and diisopropyl azodicarboxylate (1.60 g, 7.90 mmol) were added to anhydrous THF at 0° C. under a nitrogen atmosphere, and the mixture was stirred. After 4 hours, the reaction mixture was purified by silica gel chromatography to give 2-(2-(2-oxo-pyrrolidin-1-yl)-ethoxy)-isoindol-1,3-dione (1.21 g).

Workup

  1. customthe reaction mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-59280335ac874ba19d4ba217ce94749a
Source dataset
uspto-grants-2011_12
Patent number
US08084645B2

Reaction notes

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