Acetic Acid → (R)-3-(1-methyl-pyrrolidin-2-ylmethoxy)-5-trifluoromethyl-phenylamine

HRID 491599Notes

Reaction equation

HRID 491599 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][O:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([N+:19]([O-])=O)[CH:10]=1.CC(O)=O>CO.[Pd]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:10]=[C:11]([NH2:19])[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 219594761-Methyl-2-(3-nitro-5-trifluoromethyl-phenoxymethyl)-pyrrolidine

Product 1

HCID 66688753(R)-3-(1-methyl-pyrrolidin-2-ylmethoxy)-5-trifluoromethyl-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Methyl-2-(3-nitro-5-trifluoromethyl-phenoxymethyl)-pyrrolidine (2.5 g, 8.2 mmol) was dissolved in MeOH (80 ml) and HOAc (glacial, 10 mL) and placed under N2. Pd/C was added and after blanketing with H2, the mixture was shaken under H2 for 18 h at 60 psi. The catalyst was removed by filtration through Celite® and the MeOH solution was concentrated in vacuo. The residue was purified with flash chromatography (SiO2, 90:10:1 CH2Cl2:MeOH:NH4OH) to afford the title compound as a yellow liquid.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe MeOH solution was concentrated in vacuo
  3. customThe residue was purified with flash chromatography (SiO2, 90:10:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-ff017fc322a149629ca2d873850a119c
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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