Ethyl Acetate → 6-(1-Hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2069806Notes

Reaction equation

HRID 2069806 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][CH2:8][CH2:7]2)(=[O:3])[CH3:2].C[Mg+].[Br-].[Cl-].[NH4+].[C:20](OCC)(=O)C>C1COCC1>[OH:3][C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][CH2:8][CH2:7]2)([CH3:20])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 592164656-acetyl-3,4-dihydro-2H-isoquinolin-1-oneHCID 178418689HCID 178418689, compound

Product 1

HCID 592165246-(1-Hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 680 mg of 6-Acetyl-3,4-dihydro-2H-isoquinolin-1-one in 25 mL of THF cooled to 0° C. was slowly added 3.6 mL of 3.0 M MeMgBr in THF. After 1 h the mixture was poured into a solution of ammonium chloride in ice water. Ethyl acetate was added and the organic phase was partitioned, dried over sodium sulfate, filtered, and concentrated. Purification by flash chromatography afforded 380 mg of 6-(1-Hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one.

Workup

  1. customthe organic phase was partitioned
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-9dfe7c0915c24c91af2cf04d85974a46
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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