Trifluoroacetic acid → (2S,4R)-4-Fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

HRID 1961387Notes

Reaction equation

HRID 1961387 reaction equation
[F:1][C@H:2]1[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([C:14](=[O:22])[NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:14]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:22])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59436441(2S,4R)-tert-Butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 59436310(2S,4R)-4-Fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-tert-butyl 4-fluoro-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 65A (4.1 g, 12.3 mmol) in CH2Cl2 (120 mL) was added TFA (10 mL). The reaction mixture was stirred at rt overnight. After concentration in vacuo, the residue was used for the next step without purification. LC/MS [M+H]+: 211; Ret time (Method F): 0.30 min.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was used for the next step without purification
  3. custom0.30 min.

Sources & evidence

ORD record
ord-c2169ffb5ae34a3ab17f1d73b3b440f2
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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