Water → Methyl 2-{3-([tert-butoxycarbonyl)(methyl)amino]propyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 446552Notes

Reaction equation

HRID 446552 reaction equation
O[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:6][CH2:5]2.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.O.[C:50]([O:53][CH2:54]C)(=[O:52])C>CN(C)C=O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([O:18][C:17]([N:16]([CH3:24])[CH2:15][CH2:14][CH2:13][N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:50]([O:53][CH3:54])=[O:52])[CH:3]=2)[C:8]1=[O:12])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

9

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 43668911,3-Bis(phenylphosphino)propaneHCID 66671452tert-butyl [3-(6-hydroxy-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl]methylcarbamate

Product 1

HCID 66671432Methyl 2-{3-([tert-butoxycarbonyl)(methyl)amino]propyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylateYield 100%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The resulting tert-butyl [3-(6-hydroxy-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl]methylcarbamate was dissolved in a mixed solvent (11 mL) of N,N-dimethylformamide and methanol (10:1), palladium acetate (65 mg, 0.291 mmol), 1,3-diphenylphosphinopropane (120 mg, 0.291 mmol) and triethylamine (0.405 mL, 2.91 mmol) were added, and the mixture was stirred at 65° C. under a carbon monoxide atmosphere for 16 hours. After the reaction was completed, water was added to the reaction mixture, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1, v/v) to give the title compound (535 mg; yield, 100%) as a colorless oily substance.

Workup

  1. additionwere added
  2. additionwas further added
  3. customto separate the layers
  4. customThe resulting organic layer was separated
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-2155512c8dca42b8a38b361530d7c187
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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