(2-Benzylisoindolin-5-yl)methanol → Isoindolin-5-ylmethanol

HRID 334994Notes

Reaction equation

HRID 334994 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:17][OH:18])[CH:14]=2)[CH2:9]1)C1C=CC=CC=1>[Pd].C(O)C>[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([CH2:17][OH:18])=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

4

Reactant 1

HCID 19828502(2-Benzylisoindolin-5-yl)methanol

Product 1

HCID 19828514Isoindolin-5-ylmethanolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

10% Palladium on activated carbon (200 mg) was added to a solution of (2-benzyl-2,3-dihydro-1H-isoindol-5-yl)-methanol (2.39 g, 10.0 mmol) in ethanol (60 ml) and the resulting mixture was placed in a Parr apparatus, heated to 50° C. and shaken under a hydrogen atmosphere at 60 psi for 30 hours. Upon cooling to room temperature the mixture was filtered under gravity, the solids were rinsed with ethanol (2×10 ml) and the solvent removed in vacuo to afford (2,3-dihydro-1H-isoindol-5-yl)-methanol (1.49 g, 100%) as an off-white solid. 1H NMR (DMSO-d6) 7.20 (1H, s), 7.18 (1H, d), 7.12 (1H, d), 5.10 (1H, br s), 4.46 (2H, s), 4.05 (4H, s). MS: [M+H]+ 150.

Workup

  1. temperatureUpon cooling to room temperature the mixture
  2. filtrationwas filtered under gravity
  3. washthe solids were rinsed with ethanol (2×10 ml)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c4be1eebecc141fd86b984a59ef40690
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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