Methyl Ethyl Ketone → HCID 10445940, compound

HRID 2373285Notes

Reaction equation

HRID 2373285 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]2[NH:7][C:8](=[O:17])[C:9]3[C:14]([CH:15]=2)=[C:13]([CH3:16])[CH:12]=[CH:11][CH:10]=3)[CH2:2]1.Br[CH:19]([OH:21])[CH3:20].C(=O)([O-])O.[Na+].C(C(C)=O)C>O>[OH:21][CH2:19][CH2:20][N:1]1[CH2:5][CH2:4][CH:3]([C:6]2[NH:7][C:8](=[O:17])[C:9]3[C:14]([CH:15]=2)=[C:13]([CH3:16])[CH:12]=[CH:11][CH:10]=3)[CH2:2]1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 516892Sodium BicarbonateHCID 14202443Ethanol, 1-bromo-HCID 22931208HCID 22931208, compound

Product 1

HCID 10445940HCID 10445940, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the obtained (−)-3-(pyrrolidin-3-yl)-5-methyl-2H-isoquinolin-1-one (3.0 g) were added bromoethanol (8.21 g), sodium hydrogen carbonate (5.6 g), methyl ethyl ketone (84 ml) and water (8.4 ml), and the mixture was stirred under reflux for 2 hr. The reaction mixture was concentrated, extracted with methylene chloride, and the extract was washed with water, dried over magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (methanol/ethyl acetate; 2/5) and crystallized from ethyl acetate to give (−)-3-[1-(2-hydroxylethyl)pyrrolidin-3-yl]-5-methyl-2H-isoquinolin-1-one (1.5425 g).

Workup

  1. temperatureunder reflux for 2 hr
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with methylene chloride
  4. washthe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by column chromatography (methanol/ethyl acetate; 2/5)
  8. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-534fb2220a98463cb45b249c644ae9e9
Source dataset
uspto-grants-2008_12
Patent number
US07459465B2

Reaction notes

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