HCID 58902477, compound → HCID 58902228, compound

HRID 1640159Notes

Reaction equation

HRID 1640159 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1>CCO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 1

HCID 58902477HCID 58902477, compound

Product 1

HCID 58902228HCID 58902228, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-[3-amino-5-(trifluoromethyl)phenyl]-1H-pyrrole-1-carboxylate (1.99 g, 6.10 mmol) in EtOH (25 mL) was added Pd (200 mg, 10% on carbon). The reaction mixture was allowed to stir for 2 d under an atmosphere of hydrogen. The reaction mixture was filtered through a pad of Celite and washed with EtOAc. The solvents were evaporated to give tert-butyl 2-[3-amino-5-(trifluoromethyl)phenyl]pyrrolidine-1-carboxylate (1.81 g, 90%) as a white solid. LCMS: (FA) ES+ 331.3.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with EtOAc
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-8ff01b54ced0462aa90db9dcc3b2faef
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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