(R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine → (R)-1-(4-amino-2-(trifluoromethyl)benzyl)-N,N-dimethylpyrrolidin-3-amine

HRID 1640489Notes

Reaction equation

HRID 1640489 reaction equation
[CH3:1][N:2]([CH3:22])[C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:4]1>CCO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:22])[CH3:1])[CH2:4]2)=[C:10]([C:18]([F:21])([F:19])[F:20])[CH:11]=1

Participants

4

Reactant 1

HCID 66735770(R)-N,N-Dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine

Product 1

HCID 66735953(R)-1-(4-amino-2-(trifluoromethyl)benzyl)-N,N-dimethylpyrrolidin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-N,N-dimethyl-1-(4-nitro-2-(trifluoromethyl)benzyl)pyrrolidin-3-amine (1.20 g, 3.79 mmol) in 20 mL of wet EtOH was added 0.26 g of Pd/C (10% Pd on C) and the mixture shaken in a Parr apparatus (pressure reaction vessel purged thoroughly with H2 and pressure regulated at 45 psi throughout) for 2-3 h. The reaction mixture was filtered through a small pad of celite, washed with EtOAc, and the combined organics concentrated to provide a quantitative yield of a light yellow oil. This material was used directly in the next step.

Workup

  1. custompressure reaction vessel
  2. custompurged thoroughly with H2 and pressure
  3. customfor 2-3 h
  4. filtrationThe reaction mixture was filtered through a small pad of celite
  5. washwashed with EtOAc
  6. concentrationthe combined organics concentrated

Sources & evidence

ORD record
ord-c214bce0447248bf984465c906300d35
Source dataset
uspto-grants-2012_02
Patent number
US08114874B2

Reaction notes

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