Sodium Hydroxide → (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol

HRID 2207034Notes

Reaction equation

HRID 2207034 reaction equation
C([O:7][CH2:8][C@H:9]([C:15]1[C:16]([Br:27])=[C:17]2[C:22](=[CH:23][C:24]=1[CH3:25])[N:21]=[C:20]([CH3:26])[CH:19]=[CH:18]2)[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[Br:27][C:16]1[C:15]([C@H:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:8][OH:7])=[C:24]([CH3:25])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 66630692(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Product 1

HCID 66631978(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate (50.0 g, 115 mmol) in THF (600 mL) and methanol (200 mL) was added 1M NaOH solution (300 mL, excess) at 0° C. The mixture was stirred at room temperature for 16 hours, diluted with water. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product. LCMS-ESI+: calc'd for C17H22BrNO2: 352.1 (M+H+); Found: 352.1 (M+H+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c4517cced6a442d18b32c5dc0e937a4f
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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