2-Benzyl-8-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → 8-Fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445251Notes

Reaction equation

HRID 445251 reaction equation
C([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11]([F:18])[CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)C1C=CC=CC=1>CCO.CO.[OH-].[OH-].[Pd+2]>[F:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=1)[NH:8][CH2:17][CH2:16]2

Participants

5

Reactant 1

HCID 573263072-Benzyl-8-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 573263088-Fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 2-benzyl-8-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-isoquinoline (0.7 g, 2.1 mmol) in EtOH (20 mL) was stirred with 20% Pd(OH)2/C (0.20 g) under hydrogen atmosphere at 50 psi and at RT for 3 h. The reaction mixture was filtered through a celite pad and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give the pure product which was dissolved in methanol (10 mL) and neutralized by passing the solution through a Polymer Lab-HCO3 Macroporous resin cartridge, and the filtrate was concentrated to give 8-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as an off-white solid. MS (ESI pos. ion) m/z: 296 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)]
  4. customto give the pure product which
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ea6fb1c5233f41dfae350868dea08c97
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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