Water → HCID 22175943, compound

HRID 1797548Notes

Reaction equation

HRID 1797548 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[OH2:47].[O:48]1[CH2:52]CC[CH2:49]1>CO.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])=[CH:16][C:15]([C:49]([O:48][CH3:52])=[O:47])=[CH:14][CH:13]=2)=[O:39])([CH3:3])([CH3:2])[CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22176047HCID 22176047, compound

Product 1

HCID 22175943HCID 22175943, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixed solution of tert-butyl[4-(2-fluorophenyl)-2-isobutyl-1-oxo-6-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinyl]methylcarbamate (2.86 g, 5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.14 g, 0.25 mmol), triethylamine (0.77 mL, 5.5 mmol) and palladium acetate (56 mg, 0.25 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) was stirred with heating at 100° C. under a carbon monoxide atmosphere at 5 atm for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give methyl 3-[[(tert-butoxycarbonyl)amino]methyl]-4-(2-fluorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxylate (2.23 g, 92.5%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing the
  3. extractionextract with water
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-092e5a23ce7447eb98323a5da619bea8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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