Ethanol → HCID 57429663, compound

HRID 889043Notes

Reaction equation

HRID 889043 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4](CC#N)[CH2:3]1.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>>[O:24]=[C:22]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:5][CH:4]([CH2:3][C:2]([OH:1])=[O:20])[CH2:23]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 57988764HCID 57988764, compound

Product 1

HCID 57429663HCID 57429663, compoundYield 77%

Procedure

To a stirred solution of [5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-acetonitrile (0.25 g, 0.93 mmol) in ethanol (6 mL) was added sodium hydroxide solution (0.074 g, 1.86 mmol, in 3 ml water). The reaction mixture was refluxed for 3 hrs and the solvents were removed under reduced pressure, diluted with water (3 ml), washed with hexane (3×10 mL) and acidified with 2N HCl. The aqueous layer was extracted with DCM (3×15 mL) and the combined extract was washed with brine, dried with Na2SO4, evaporated under reduced pressure to obtain [5-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidin-3-yl]-acetic acid (0.2 g, 77%) as an off white semi solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hrs
  2. customthe solvents were removed under reduced pressure
  3. additiondiluted with water (3 ml)
  4. washwashed with hexane (3×10 mL)
  5. extractionThe aqueous layer was extracted with DCM (3×15 mL)
  6. extractionthe combined extract
  7. washwas washed with brine
  8. dry with materialdried with Na2SO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b9f27aa036a418db7d6e3becd002867
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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