Water → 6-(3-Fluoro-benzyloxy)-2-(2-methoxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2415440Notes

Reaction equation

HRID 2415440 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH:18]([CH3:21])[CH2:19][OH:20])[CH2:11][CH2:10]2.[H-].[Na+].[CH3:27]I.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH:18]([CH3:21])[CH2:19][O:20][CH3:27])[CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 226419476-(3-Fluoro-benzyloxy)-2-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 226419416-(3-Fluoro-benzyloxy)-2-(2-methoxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-oneYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-(3-Fluoro-benzyloxy)-2-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one (0.020 g, 0.061 mmol) and sodium hydride (55%, 2.2 mg, 0.067 mmol) in N,N′-dimethylformamide (0.2 mL), methyl iodide (0.009 mL, 0.152 mmol) was added. Water was added and the reaction was extracted with ethyl acetate. After drying of the organic layer with MgSO4, filtration and evaporation, the residue was purified by chromatography (SiO2, hexane/ethyl acetate 9:1 v:v) to give the title compound as a white solid (0.0095 g, 43%). MS: m/e=344.4 (M+H+).

Workup

  1. additionwas added
  2. extractionthe reaction was extracted with ethyl acetate
  3. dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation
  4. customthe residue was purified by chromatography (SiO2, hexane/ethyl acetate 9:1 v:v)

Sources & evidence

ORD record
ord-18bbac85ec934774ad02a2ce1af52ec8
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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