HCID 22175437, compound → HCID 22176015, compound

HRID 1797602Notes

Reaction equation

HRID 1797602 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25](N(OC)C)=[O:26])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[CH3:37][Mg]Br>O1CCCC1.C(OCC)C>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25](=[O:26])[CH3:37])=[CH:14][CH:13]=2)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 22175437HCID 22175437, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22176015HCID 22176015, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl(2-isobutyl-6-{[methoxy(methyl)amino]carbonyl}-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.175 g, 0.355 mmol) was dissolved in tetrahydrofuran (5 mL) and a solution (0.15 mL, 0.43 mmol) of 3 M methyl magnesium bromide in diethyl ether was added dropwise under ice-cooling. This mixture was stirred at room temperature for 1 h and quenched with saturated aqueous ammonium chloride solution (5 mL). The whole was extracted with ethyl acetate (10 mL), and the organic layer was washed once each with 0.1 M aqueous citric acid solution (10 mL), saturated aqueous sodium hydrogencarbonate (10 mL) and saturated brine (10 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v)) to give tert-butyl(6-acetyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.132 g, 83%) as a colorless powder.

Workup

  1. temperaturecooling
  2. customquenched with saturated aqueous ammonium chloride solution (5 mL)
  3. extractionThe whole was extracted with ethyl acetate (10 mL)
  4. washthe organic layer was washed once each with 0.1 M aqueous citric acid solution (10 mL), saturated aqueous sodium hydrogencarbonate (10 mL) and saturated brine (10 mL)
  5. dry with materialdried over anhydrous magnesium sulfate (12 g)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v))

Sources & evidence

ORD record
ord-dbd6f9dc9a584b9b8197de4174f67f37
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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