Methanol → tert-Butyl 5-bromo-1-oxo-1,3-dihydro-2H-isoindole-2-carboxylate

HRID 601660Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][CH2:5]2.[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13].CO>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, 70 mg of 5-bromo-1-oxo-isoindoline was dissolved in 2 ml of tetrahydrofuran, cooled down to 0° C., and then 4 mg of N,N-dimethylaminopyridine and 144 mg of di-tert-butylcarbonate were added. The mixture was stirred at room temperature for 30 min. Methanol was added to the reaction solution, and the solvents were distilled outunder reduced pressure. Water was added to the residues, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2), to obtain 51.2 mg of the above compound as a white solid.

Workup

distillationthe solvents were distilled outunder reduced pressure
additionWater was added to the residues
extractionextracted with ethyl acetate
washEthyl acetate layer was washed with saturated saline solution
dry with materialdried with anhydrous sodium sulfate
distillationAfter distilling out the solvents under reduced pressure
customthe residues were separated
custompurified by silicagel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record: ord-f97bee4de3f744e89a8f2519c789c528
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902369B2

Reaction notes

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