Phthalimide → (s)-2-(2-Hydroxybutyl)isoindoline-1,3-dione

HRID 2387865Notes

Reaction equation

HRID 2387865 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].[O:12]1[C@@H:14]([CH2:15][CH3:16])[CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[OH:12][C@@H:14]([CH2:15][CH3:16])[CH2:13][N:9]1[C:7](=[O:8])[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:10]1=[O:11]

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 10898629(2S)-2-Ethyloxirane

Product 1

HCID 11424533(s)-2-(2-Hydroxybutyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 1,2-Benzenedicarboximide (4.29 g) in DMF (10 ml), (S)-(−)-1,2-epoxybutane (2.1 g) was added followed by K2CO3 (4.03 g) and heated at 60° C. for 48 h. The reaction was diluted with water, extracted with EtOAc, dried and solvent removed to give the subtitle compound as a white solid, 1.8 g.

Workup

  1. extractionextracted with EtOAc
  2. customdried
  3. customsolvent removed

Sources & evidence

ORD record
ord-d0f288d90bfe42a493cf9791ccb7f4ab
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

Loading…