(2,4-Bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone → (1,3-Dihydro-isoindol-2-yl)-(2,4-dihydroxy-5-trifluoromethyl-phenyl)-methanone

HRID 424091Notes

Reaction equation

HRID 424091 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]([F:26])([F:25])[F:24])=[CH:11][C:10]=1[C:27]([N:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1)=[O:28])C1C=CC=CC=1>CO.[Pd]>[CH2:30]1[C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:37][N:29]1[C:27]([C:10]1[CH:11]=[C:12]([C:23]([F:26])([F:25])[F:24])[C:13]([OH:15])=[CH:14][C:9]=1[OH:8])=[O:28]

Participants

4

Reactant 1

HCID 59263097(2,4-Bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

Product 1

HCID 11955511(1,3-Dihydro-isoindol-2-yl)-(2,4-dihydroxy-5-trifluoromethyl-phenyl)-methanoneYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2,4-bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone (140 mg, 0.28 mmol) in methanol (5 mL) was hydrogenated at atmospheric pressure over 10% palladium on charcoal (34 mg) for 4 hours. A further portion of catalyst was added (31 mg) and hydrogenation continued for a further 1.5 hours. The mixture was filtered through Celite, eluting with methanol, then the filtrate was concentrated in vacuo to afford the title compound as a white solid (91 mg, quant.). 1H NMR (DMSO-d6) 10.79 (1H, s), 10.70 (1H, s), 7.40-7.35 (2H, m), 7.31-7.35 (3H, m), 6.61 (1H, s), 4.79 (2H, br.s), 4.68 (2H, br.s). MS: [M+H]+ 324.

Workup

  1. additionA further portion of catalyst was added (31 mg) and hydrogenation
  2. filtrationThe mixture was filtered through Celite
  3. washeluting with methanol
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3d7341686039489bb538f0143ab89dd7
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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