Sodium Hydroxide → (1S,4S)-1-(2,2-difluoroethyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylic acid

HRID 2067844Notes

Reaction equation

HRID 2067844 reaction equation
[F:1][CH:2]([F:20])[CH2:3][C@@:4]1([C:16]([O:18]C)=[O:17])[CH2:8][C@H:7]([N:9]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:15])[CH:6]=[CH:5]1.[OH-].[Na+]>CO>[F:20][CH:2]([F:1])[CH2:3][C@@:4]1([C:16]([OH:18])=[O:17])[CH2:8][C@H:7]([N:9]2[C:10]([CH3:15])=[CH:11][CH:12]=[C:13]2[CH3:14])[CH:6]=[CH:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58305966methyl (1S,4S)-1-(2,2-difluoroethyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylate

Product 1

HCID 58305912(1S,4S)-1-(2,2-difluoroethyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (1S,4S)-1-(2,2-difluoroethyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylate (7.54 g, 26.6 mmol) in methanol (60 ml) was treated with 2.5N NaOH (15 ml, 37.5 mmol) and stirred at room temperature for 22 hours. The methanol was removed under reduced pressure and the residue partitioned between diethyl ether and water. The layers were separated and the aqueous was acidified with 4N HCl, extracted with ethyl acetate, washed with brine, dried over MgSO4, and concentrated under reduced pressure to give (1S,4S)-1-(2,2-difluoroethyl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-2-ene-1-carboxylic acid as a brown oil (6.59 g, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 6.12-6.09 (1H), 6.07-6.05 (0.25H), 5.99-5.96 (1H), 5.93-5.91 (0.5H), 5.79-5.76 (0.25H), 5.74 (2H), 5.38-5.32 (1H), 2.54-2.46 (2H), 2.43-2.25 (2H), 2.20 (6H).

Workup

  1. customThe methanol was removed under reduced pressure
  2. customthe residue partitioned between diethyl ether and water
  3. customThe layers were separated
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e53221bcfc047959058e9d2ee526e83
Source dataset
uspto-grants-2012_10
Patent number
US08293903B2

Reaction notes

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