HCID 67520356, compound → HCID 63163866, compound

HRID 1925405Notes

Reaction equation

HRID 1925405 reaction equation
[CH3:1][N:2]([CH3:21])[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:4]1>CO.[Pd]>[NH2:18][C:9]1[CH:10]=[C:11]([C:14]([F:15])([F:16])[F:17])[CH:12]=[CH:13][C:8]=1[N:5]1[CH2:6][CH2:7][CH:3]([N:2]([CH3:21])[CH3:1])[CH2:4]1

Participants

4

Reactant 1

HCID 67520356HCID 67520356, compound

Product 1

HCID 63163866HCID 63163866, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-N,N-dimethyl-1-(2-nitro-4-(trifluoromethyl)phenyl)pyrrolidin-3-amine (1.75 g, 5.77 mmol) in MeOH (60 mL) was added 10% Pd/C (0.30 g, 0.29 mmol). H2 gas was bubbled through the solution for 5 minutes, and the reaction was stirred at RT under an atmosphere of H2 gas. The reaction was monitored by LCMS for disappearance of starting material and formation of product. The mixture was filtered through celite with MeOH, and concentrated to afford the product as an orange/red oil.

Workup

  1. customH2 gas was bubbled through the solution for 5 minutes
  2. filtrationThe mixture was filtered through celite with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5f8fbb06ecf04ecf8efd30fbfc71a8ed
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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