Hydrochloric Acid → (S)-Vigabatrin

HRID 248198Notes

Reaction equation

HRID 248198 reaction equation
C(C1C=C(C(C)(C)C)C=CC=1O[C@H](C)C([N:19]1[C@H:23]([CH:24]=[CH2:25])[CH2:22][CH2:21][C:20]1=[O:26])=O)(C)(C)C.[OH-:28].[K+].Cl>O>[NH2:19][C@H:23]([CH:24]=[CH2:25])[CH2:22][CH2:21][C:20]([OH:26])=[O:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57295025(5S)-N-((2R)-2-(2,4-di-t-butylphenyloxy)propanoyl)-5-ethenylpyrrolidin-2-one

Product 1

HCID 10219440(S)-Vigabatrin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of (5S)-N-((2R)-2-(2,4-di-t-butylphenyloxy)-propanoyl)-5-ethenylpyrrolidin-2-one (19a, 1.0 g, 2.5 mmol) and 87% potassium hydroxide (317 mg, 5.7 mmol) in water (2 mL) is refluxed for 1.5 hours. The solution is allowed to cool to room temperature. Water is added (15 mL) and the solution is acidified to pH 7 with concentrated hydrochloric acid and extracted with diethyl ether (3×10 mL) to remove the chiral auxiliary. The aqueous solution is then acidified to pH 5.5 with concentrated hydrochloric acid and extracted with diethyl ether (3×15 mL). The second series of organic extracts are combined and dried (MgSO4). Concentration by rotary evaporation affords (4S)-4-amino-5-hexenoic acid (B).

Workup

  1. extractionextracted with diethyl ether (3×10 mL)
  2. customto remove the chiral auxiliary
  3. extractionextracted with diethyl ether (3×15 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration
  6. customby rotary evaporation

Sources & evidence

ORD record
ord-43514b78e01e4b0daf9225fbe75dd363
Source dataset
uspto-grants-1993_05
Patent number
US05208345

Reaction notes

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