2-Benzyl-1,1,3,3-tetramethylisoindoline → 1,1,3,3-Tetramethylisoindoline

Participants

Reaction Steps

(Griffiths, P. G. et al. Synthesis of the radical scavenger 1,1,3,3-tetramethylisoindolin-2-yloxyl. Aust. J. Chem. 1983, 36, 397-401; Chan, K. S. et al. Reactions of nitroxides with metalloporphyrin alkyls bearing beta hydrogens: aliphatic carbon-carbon bond activation by metal centered radicals. J. Organomet. Chem. 2008, 693, 399-407). The protected benzyl-amine 16 (1.864 g, 7.02 mmol) was dissolved in AcOH (34 mL) in a Parr flask, and 10% Pd/C (169.5 mg) was added. (The reaction was split in 3 batches.) The flask was placed in a high pressure reactor. The reactor was charged with H2 and purged for 5 cycles and was finally pressurized with H2 at 4 bars (60 psi). After stirring at rt for 3 h, the reaction mixture was filtered through Celite, and the solvent removed in vacuo. The resulting residue was dissolved in water (5 mL) and the solution neutralized with 2.5N NaOH (pH 11.5), and extracted with Et2O (3×50 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to yield 1.165 g (95%) of the crude title compound as slightly yellow crystals. mp 36.0-36.5° C. 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2 H), 7.18-7.11 (m, 2H), 1.86 (bs, 1H), 1.48 (s, 12H).

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