HCID 68410552, compound → HCID 59410098, compound

HRID 404600Notes

Reaction equation

HRID 404600 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:8]=2)[CH2:3]1>[Pd]>[CH3:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:16]([F:19])([F:17])[F:18])[CH:8]=2)[CH2:3]1

Participants

3

Reactant 1

HCID 68410552HCID 68410552, compound

Product 1

HCID 59410098HCID 59410098, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with (S)-3-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (1 g, 3.646 mmol) and palladium (100 mg, 0.9397 mmol) was flushed with N2 followed by evacuating under vacuum. Methanol (10 mL) was added under inert atmosphere followed by evacuating under vacuum. The reaction placed under an atmosphere of hydrogen and the reaction was stirred overnight. Pd/C was removed by filtration and solvent was removed under reduced pressure to give (S)-4-(3-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline (850 mg, 95%) MS 245.0 m/z (MH+).

Workup

  1. customwas flushed with N2
  2. customby evacuating under vacuum
  3. additionMethanol (10 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. customPd/C was removed by filtration and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-5d2cbcd3a05143a495be4608e9db7121
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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