Phthalimide → 2-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dione

HRID 2427253Notes

Reaction equation

HRID 2427253 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>>[O:6]=[C:1]1[CH2:5][CH2:4][CH:3]([N:11]2[C:7](=[O:17])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10]2=[O:12])[CH2:2]1

Participants

3

Reactant 2

HCID 6809PhthalimideHCID 135882-Cyclopenten-1-one

Product 1

HCID 545940982-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dione

Procedure

In Scheme II, Step A, cyclopentenone (8) is reacted with phthalimide in a Michael addition to give (±)-2-(3-oxo-cyclopentyl)-isoindole-1,3-dione (9). The reaction is performed in methanol/2N Na2CO3 in a ratio of 10/1 by volume preferably at ambient temperature using conditions similar to those described by O. Nowitzki, et. al. in Tetrahedron 1996, 52, 11799-11810. The product is isolated by addition of water and (9) obtained as a white solid.

Sources & evidence

ORD record
ord-96a6efc97ffb42529c21252ce826e8fa
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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