(+/-)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole → (+/-)-2-(2,3-dihydro-1H-isoindol-1-yl)-4-fluoro-phenol

HRID 2036239Notes

Reaction equation

HRID 2036239 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[O:24]CC1C=CC=CC=1)C1C=CC=CC=1>CCO.[Pd]>[CH:9]1([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[OH:24])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

4

Reactant 1

HCID 86682590(+/-)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole

Product 1

HCID 66654979(+/-)-2-(2,3-dihydro-1H-isoindol-1-yl)-4-fluoro-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution under N2 of (±)-2-benzyl-1-(2-benzyloxy-5-fluoro-phenyl)-2,3-dihydro-1H-isoindole (181 mg, 0.44 mmol, 1.0 eq.) in EtOH (20 mL), palladium on activated carbon (10 wt. %, 60 mg) was added. The flask was evacuated and backfilled with H2 (3×). The black suspension was stirred at r.t. under an H2-atmosphere for 18 hours. The suspension was filtered through Celite, the Celite rinsed with EtOH. The filtrate was concentrated in vacuo. The residue was filtered and then purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give (±)-2-(2,3-dihydro-1H-isoindol-1-yl)-4-fluoro-phenol.

Workup

  1. customThe flask was evacuated
  2. filtrationThe suspension was filtered through Celite
  3. washthe Celite rinsed with EtOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. filtrationThe residue was filtered
  6. custompurified by prep
  7. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-c2bdff25dc2e49da8ef0f0ce57962d07
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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