Isoindoline → 3-Amino-1-(1,3-dihydroisoindol-2-yl)-3-methylbutan-1-one
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[NH2:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13](O)=[O:14].Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1>CN(C)C=O>[NH2:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2,3-Dihydro-1H-isoindole (543 mg) and 3-amino-3-methylbutanoic acid (700 mg) were dissolved in N,N-dimethylformamide (30 ml). N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (876 mg) and hydroxybenzotriazole (698 mg) were added thereto at 0° C., and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic phase was separated, and the aqueous phase was adjusted to pH 9 by adding a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure to give the title compound (0.60 g, Y.:60%) as a brown oily matter.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl acetate
- additionwere added to the residue
- customThe organic phase was separated
- additionby adding a saturated sodium bicarbonate solution
- extractionextracted with ethyl acetate
- dry with materialThe extract was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5df6aa48d0714eeaaf4457e442735942
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07345180B2
Reaction notes
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