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

HRID 471967Notes

Reaction equation

HRID 471967 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>CO.[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

4

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)anilineYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (12.0 g, 43.68 mmol) in methanol (75 mL) was added 10% Pd/C (1.2 g). The reaction was stirred under H2 atmosphere for 16 h. The mixture was filtered through a pad of Celite and concentrated. Purification by silica gel chromatography (0-100% ethyl acetate/hexanes) provided (S)-4-(2-methylpyrrolidin-1-yl)-2-(trifluoromethyl)aniline as a brown oil (10.5 g, 98% yield). LC/MS m/z 245.1 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-85f41e7867604b63a323215a6e6c533d
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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