1-[1-(4-Benzyloxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone → 2,2,2-trifluoro-1-[1-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanone

HRID 397072Notes

Reaction equation

HRID 397072 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH3:26])=[CH:22][CH:23]=3)[CH2:18][CH2:17][N:16]2[C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCO.[Pd]>[F:31][C:28]([F:29])([F:30])[C:27]([N:16]1[CH2:17][CH2:18][C:19]2[C:24](=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH:15]1[C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)=[O:32]

Participants

4

Reactant 1

HCID 181724231-[1-(4-Benzyloxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone

Product 1

HCID 120859392,2,2-trifluoro-1-[1-(4-hydroxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]ethanoneYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-[1-(4-Benzyloxyphenyl)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone (26.97 g, 61.1 mmol) was hydrogenated using 10% Pd/C (1.000 g) in EtOH (300 ml) at an initial pressure of 44 psi (˜300,000 Pa) at rt for 6 hr. The reaction mixture was filtered through a pad of Celite to remove the catalyst and the filtrate was evaporated in vacuo to give 18.98 g (88% yield) of white solid.

Workup

  1. customat rt
  2. customfor 6 hr
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. customto remove the catalyst
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1132e34817d24fbe8b8a46f22f6806c4
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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