Methanol → HCID 59238292, compound

HRID 220186Notes

Reaction equation

HRID 220186 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:20]O>O=S(Cl)Cl>[CH3:20][O:10][C:9](=[O:11])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH3:19]

Participants

4

Reactant 2

HCID 887MethanolHCID 59238295HCID 59238295, compound

Product 1

HCID 59238292HCID 59238292, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To the solution of 2-(4-bromo-phenyl)-4-(1-methyl-pyrrolidin-2-yl)-butyric acid in MeOH (60 mL), SOCl2 (2 mL) was added at 0 degrees Celsius, then the mixture refluxed for 5 h. After cooling, the solution was evaporated to dryness under reduced pressure, then EtOAc was added, the organic layer was washed with aq. NaHCO3, dried with MgSO4, and evaporated to give an oil. MS: calc'd 340 (MH+), exp 340 (MH+).

Workup

  1. temperaturethe mixture refluxed for 5 h
  2. temperatureAfter cooling
  3. customthe solution was evaporated to dryness under reduced pressure
  4. additionEtOAc was added
  5. washthe organic layer was washed with aq. NaHCO3
  6. dry with materialdried with MgSO4
  7. customevaporated
  8. customto give an oil

Sources & evidence

ORD record
ord-b8810eded4ae4ae5b4949c0a8b113fc8
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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