benzyl 1-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate → 1-(6-(Trifluoromethyl)pyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline

HRID 445384Notes

Reaction equation

HRID 445384 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[N:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2C(OCC2C=CC=CC=2)=O)=[CH:5][CH:4]=1>CO.[Pd]>[F:30][C:2]([F:1])([F:29])[C:3]1[N:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 59536315benzyl 1-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 595362781-(6-(Trifluoromethyl)pyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 1-(6-(trifluoromethyl)pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (90 mg, 218 μmol) in MeOH (3 mL) at RT under N2 was added 10% palladium on carbon (46 mg, 44 μmol) and suspension was sparged with H2 15 min. The reaction was stirred under H2 at RT 3.5 h. The reaction was filtered through a pad of Celite® (2×5 mL EtOAc wash) and concentrated to give 1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline which was carried on to the next step without purification.

Workup

  1. customwas sparged with H2 15 min
  2. filtrationThe reaction was filtered through a pad of Celite® (2×5 mL EtOAc wash)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2a862904f24e4f64b79ab743f10a0df6
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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