tert-Butyl ((3-oxoisoindolin-5-yl)methyl)carbamate → 6-(Aminomethyl)-2,3-dihydro-1H-isoindol-1-one
Reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH2:14][NH:13][C:12]2=[O:18])(C)(C)C>Cl>[NH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15]([CH2:14][NH:13][C:12]2=[O:18])=[CH:16][CH:17]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of the product of Step 2 (100 g, 0.38 mol) and HCl (dissolved in MeOH, 3 M, 500 ml) was stirred overnight. Removal of the solvent gave a solid which was washed with Et2O and dried to afford 6-(aminomethyl)-2,3-dihydro-1H-isoindol-1-one (57 g, 76% yield). 1H-NMR (300 MHz, D2O) δ: 7.69-7.67 (m, 1H), 7.52 (s, 1H), 7.45-7.43 (m, 1H), 4.39 (s, 2H), 4.17 (s, 2H).
Workup
- customRemoval of the solvent
- customgave a solid which
- washwas washed with Et2O
- customdried
Sources & evidence
- ORD record
- ord-52fe6ca7f23e43cb82927a0f075f8f81
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
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