Pivaloyl chloride → (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-hydroxyethyl pivalate

HRID 2207052Notes

Reaction equation

HRID 2207052 reaction equation
[Br:1][C:2]1[C:11]([C@H:12]([OH:15])[CH2:13][OH:14])=[C:10]([CH3:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:17])=[N:7]2.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>ClCCl.N1C=CC=CC=1>[C:20]([O:14][CH2:13][C@H:12]([C:11]1[C:2]([Br:1])=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:16])[N:7]=[C:6]([CH3:17])[CH:5]=[CH:4]2)[OH:15])(=[O:21])[C:19]([CH3:24])([CH3:23])[CH3:18]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 66633145(S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol

Product 1

HCID 66631779(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-hydroxyethyl pivalate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-(5-bromo-2,7-dimethylquinolin-6-yl)ethane-1,2-diol (290 mg, 0.98 mmol) in dichloromethane (12 mL) and pyridine (2 mL) was added trimethyl acetylchloride (0.24 mL, 1.97 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours, and quenched with slow addition of NaHCO3 solution. 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 (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-hydroxyethyl pivalate. LCMS-ESI+ (m/z): [M+H]+ calc'd for C18H23BrNO3: 380.1; Found: 380.2.

Workup

  1. customquenched with slow addition of NaHCO3 solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record
ord-74ba0a8e0a9b4f858e2141a527e5d981
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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