1-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine → 3-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)aniline

HRID 1181353Notes

Reaction equation

HRID 1181353 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:4]=1[O:5][CH2:6][C:7]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:9])[CH3:8]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([CH:16]=[CH:15][C:4]=1[O:5][CH2:6][C:7]([CH3:9])([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:8])[NH2:19]

Participants

4

Reactant 1

HCID 589807741-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine

Product 1

HCID 589808333-Methoxy-4-(2-methyl-2-pyrrolidin-1-ylpropoxy)anilineYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(2-Methoxy-4-nitrophenoxy)-1,1-dimethylethyl]pyrrolidine (0.075 g, 0.2551 mmol) was dissolved in EtOAc (10 mL). 10% Pd/C (0.007 g) was added and the reaction hydrogenated under 1 atm of H2. The reaction was stirred for 18 h, filtered through celite and the celite washed with EtOAc (3×30 mL). The combined organics were concentrated to afford 0.063 g (0.2386 mmol, 93%) of the product. 1H NMR (CDCl3) δ 6.80 (d, 1H, J=8.4 Hz), 6.22 (s, 1H), 6.18 (d, 1H, J=8.3 Hz), 3.78 (s, 3H), 3.50 (bs, 2H), 2.68 (bs, 6H), 1.78 (bs, 4H), 1.22 (s, 6H).

Workup

  1. customthe reaction hydrogenated under 1 atm of H2
  2. filtrationfiltered through celite
  3. washthe celite washed with EtOAc (3×30 mL)
  4. concentrationThe combined organics were concentrated

Sources & evidence

ORD record
ord-e5450dc4bd14455e9073c2f455da2de1
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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