(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine → (S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline

HRID 1915487Notes

Reaction equation

HRID 1915487 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([C:16]([F:19])([F:18])[F:17])[CH:8]=1>[Pd]>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:16]([F:18])([F:17])[F:19])[CH:8]=1

Participants

3

Reactant 1

HCID 59395009(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine

Product 1

HCID 59395038(S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (2.45 g, 8.9 mmol) and palladium on carbon (245 mg, 10 wt %) was flushed with N2 followed by evacuating under vacuum. Methanol (15 mL) was added under inert atmosphere followed by evacuating under vacuum. The reaction mixture was stirred overnight under an atmosphere of H2. The palladium catalyst was removed by filtration and solvent was removed under reduced pressure to give (S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl) aniline in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ 6.78 (d, J=8.8 Hz, 1H), 6.70-6.67 (m, 1H), 6.47 (d, J=2.7 Hz, 1H), 4.68 (s, 2H), 3.76-3.69 (m, 1H), 3.32-3.27 (m, 1H), 3.02-2.96 (m, 1H), 2.05-1.94 (m, 2H), 1.93-1.84 (m, 1H), 1.64-1.58 (m, 1H), 1.05 (d, J=6.1 Hz, 3H). LC/MS: m/z 245.1 (M+H)+ at 0.48 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas flushed with N2
  2. customby evacuating under vacuum
  3. additionMethanol (15 mL) was added under inert atmosphere
  4. customby evacuating under vacuum
  5. customThe palladium catalyst was removed by filtration and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-60137de3192c4ba38990f5fe53f1fa1d
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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