Water → HCID 22175450, compound

HRID 1797707Notes

Reaction equation

HRID 1797707 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:11](=[O:30])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24](N(OC)C)=[O:25])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].O1CCC[CH2:37]1.C[Mg]Br.O>O1CCCC1>[C:1]([O:5][C:6](=[O:35])[NH:7][CH2:8][C:9]1[N:10]([CH2:31][CH:32]([CH3:33])[CH3:34])[C:11](=[O:30])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24](=[O:25])[CH3:37])=[CH:14][CH:13]=2)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 86592080HCID 86592080, compoundHCID 178420675HCID 178420675, compound

Product 1

HCID 22175450HCID 22175450, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl(4-butoxy-2-isobutyl-6{[methoxy(methyl)amino]carbonyl}-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.49 g, 1 mmol) in tetrahydrofuran (10 ml) was added 1N methylmagnesium bromide tetrahydrofuran solution (5 ml) at 0° C. The mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl(6-acetyl-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.37 g, 84.1%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4aaa14bdce544d808f883a2ce275cc11
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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