Water → HCID 22176132, compound

HRID 1797485Notes

Reaction equation

HRID 1797485 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:11](=[O:25])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([OH:24])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:33][CH2:34][CH3:35].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:11](=[O:25])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([O:24][CH2:33][CH2:34][CH3:35])=[CH:14][CH:13]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 86592068HCID 86592068, compound

Product 1

HCID 22176132HCID 22176132, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl(4-butoxy-6-hydroxy-2-neopentyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.52 g, 1.2 mmol), 1-bromopropane (0.16 ml, 1.2 mmol) and potassium carbonate (0.16 g, 1.2 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 12 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(4-butoxy-2-neopentyl-1-oxo-6-propoxy-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.50 g, 89.3%) as an amorphous.

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-c1cb35c2bdb34887b9783e029ca5daa1
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…