Ammonia → (4S)-BrivaracetaM

HRID 229853Notes

Reaction equation

HRID 229853 reaction equation
[NH3:1].[O:2]=[C:3]1[CH2:7][C@H:6]([CH2:8][CH2:9][CH3:10])[CH2:5][N:4]1[C@@H:11]([CH2:16][CH3:17])[C:12](OC)=[O:13]>O>[O:2]=[C:3]1[CH2:7][C@H:6]([CH2:8][CH2:9][CH3:10])[CH2:5][N:4]1[C@@H:11]([CH2:16][CH3:17])[C:12]([NH2:1])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86594634HCID 86594634, compound

Product 1

HCID 9855859(4S)-BrivaracetaM

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

Ammonia gas was condensed in 2 ml water at 0-5° C. and the temperature of the system was maintained at 0-5° C. 0.68 g of methyl (2S)-2-[2-oxo-(4S)-4-propyl-1-pyrrolidinyl]butanoate obtained such as described above was then added dropwise, maintaining the reaction mixture at 0-5° C. The system was then stirred for 6 hrs, with TLC indicating completion of reaction. After standing overnight at ambient temperature the reaction mixture was concentrated at 40° C. under vacuum and further dried by azyeotropic distillation with toluene to give 150 mg of crude (2S)-2-[2-oxo-(4S)-4-propyl-1-pyrrolidinyl]butanamide.

Workup

  1. additionabove was then added dropwise
  2. temperaturemaintaining the reaction mixture at 0-5° C
  3. customcompletion of reaction
  4. waitAfter standing overnight at ambient temperature
  5. concentrationthe reaction mixture was concentrated at 40° C. under vacuum
  6. dry with materialfurther dried by azyeotropic distillation with toluene

Sources & evidence

ORD record
ord-89e5b76b77954d2d9ed1c8a52d07d5af
Source dataset
uspto-grants-2009_07
Patent number
US07563912B2

Reaction notes

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