HCID 11404450, compound → Dimethyl 2-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)pentanedioate

HRID 1009088Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=S)[N:3]1[CH:12]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:13]([O:15][CH3:16])=[O:14].C(Cl)Cl.CC[O:28]C(C)=O>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:28])[N:3]1[CH:12]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:13]([O:15][CH3:16])=[O:14]

Participants

Reactant 2

HCID 11404450HCID 11404450, compound

HCID 21226138Dichloromethane ethylacetate

Product 1

HCID 272791Dimethyl 2-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)pentanedioate

Procedure

Dimethyl 2-(1,3-dihydro-1-oxo-3-thioxo-2H-isoindol-2-yl) -pentanedioate (208) and Dimethyl 2-(1,3-dihydro-1,3-dithioxo-2H-isoindol-2-yl)-pentanedioate (209). A mixture of compound 207 (144 mg, 0.47 mmol) and LR (191 mg, 0.47 mmol) in toluene was stirred in a 110° C. oil bath for 10 h. The solvent was then evaporated and the residue was purified by column chromatography, (silica gel) using CH2Cl2 as the eluent, to obtain compound 209 (17 mg, 11%) as a dark red oil. Thereafter, using CH2Cl2:EtOAc (10:1) as the eluent the more polar component 208 (105 mg, 70%) was obtained as a red oil.

Workup

customwas obtained as a red oil

Sources & evidence

ORD record: ord-88417c9874254f3e877d802221832d2f
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973057B2

Reaction notes

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