Trifluoroacetic acid → 4-Benzyloxy-1-[2-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-1H-pyridin-2-one

HRID 564182Notes

Reaction equation

HRID 564182 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][CH2:19][N:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:22][C:21]3=[O:34])=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][N:20]([CH2:19][CH2:18][C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9]3)=[CH:14][CH:13]=2)[C:21](=[O:34])[CH:22]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 580427667-[2-(4-Benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 580427534-Benzyloxy-1-[2-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 400 mg (0.87 mmol) 7-[2-(4-benzyloxy-2-oxo-2H-pyridin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example 24.1) in 5.0 mL DCM is added at RT 0.5 mL trifluoroacetic acid. The reaction mixture is stirred overnight at RT and is neutralized with aqueous 5% NaHCO3-solution. The layers are separated, the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is elutriated in tertbutylmethyether, the precipitate is collected and dried.

Workup

  1. customThe layers are separated
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customthe precipitate is collected
  7. customdried

Sources & evidence

ORD record
ord-fc0045f2564146689aa95414b83c5bf2
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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