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

HRID 1505293Notes

Reaction equation

HRID 1505293 reaction equation
C([N:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1([CH3:20])[CH3:19])C1C=CC=CC=1>CC(O)=O.[Pd]>[CH3:17][C:16]1([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:20])([CH3:19])[NH:8]1

Participants

4

Reactant 1

HCID 129238792-Benzyl-1,1,3,3-tetramethylisoindoline

Product 1

HCID 6410271,1,3,3-TetramethylisoindolineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(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 splited 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, 2 H), 1.86 (bs, 1 H), 1.48 (s, 12 H).

Workup

  1. additionwas added
  2. custom(The reaction was splited in 3 batches)
  3. customThe flask was placed in a high pressure reactor
  4. additionThe reactor was charged with H2
  5. custompurged for 5 cycles
  6. filtrationthe reaction mixture was filtered through Celite
  7. customthe solvent removed in vacuo
  8. dissolutionThe resulting residue was dissolved in water (5 mL)
  9. extractionextracted with Et2O (3×50 mL)
  10. dry with materialThe combined organic layers were dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0afe1af5874444ab9a5e7c1fe67cd262
Source dataset
uspto-grants-2015_12
Patent number
US09216976B2

Reaction notes

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