Trifluoroacetic acid → (3S,5R)-5-(3-fluorophenyl)pyrrolidine-3-carbonitrile 2,2,2-trifluoroacetate

HRID 513025Notes

Reaction equation

HRID 513025 reaction equation
[C:1]([C@@H:3]1[CH2:7][N:6](C(OC(C)(C)C)=O)[C@@H:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[CH2:4]1)#[N:2].[C:22]([OH:28])([C:24]([F:27])([F:26])[F:25])=[O:23]>C(Cl)Cl>[F:25][C:24]([F:27])([F:26])[C:22]([OH:28])=[O:23].[F:21][C:17]1[CH:16]=[C:15]([C@@H:5]2[NH:6][CH2:7][C@@H:3]([C:1]#[N:2])[CH2:4]2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68282507(2R,4S)-tert-butyl 4-cyano-2-(3-fluorophenyl)-pyrrolidine-1-carboxylate

Product 1

HCID 66691683(3S,5R)-5-(3-fluorophenyl)pyrrolidine-3-carbonitrile 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4S)-tert-butyl 4-cyano-2-(3-fluorophenyl)-pyrrolidine-1-carboxylate (I-30) (72 mg, 0.25 mmol) in DCM (0.5 mL) was added TFA (0.5 mL) with stirring. After 1 hour the volatile organics were removed under reduced pressure. The residue was triturated with Et2O and the resulting solids collected and dried under vacuum to give (3S,5R)-5-(3-fluorophenyl)pyrrolidine-3-carbonitrile 2,2,2-trifluoroacetate (I-31), which was used without purification. MS m/z 191.1 (M+1)+.

Workup

  1. customAfter 1 hour the volatile organics were removed under reduced pressure
  2. customThe residue was triturated with Et2O
  3. customthe resulting solids collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d3a9e4e9b47b46099451b3c0f42e591c
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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