HCID 58307330, compound → HCID 58307156, compound

HRID 448402Notes

Reaction equation

HRID 448402 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:14]=[CH:15][C:16]=1[NH2:17]

Participants

5

Reactant 2

HCID 58307330HCID 58307330, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58307156HCID 58307156, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[2-(3-methoxy-4-nitro-phenoxy)-ethyl]-pyrrolidine (2.2 g, 8.3 mmol) and 5% Pd—C (0.4 g) in ethyl acetate (70 mL) was shaken under 50 psi of hydrogen for 22 hours. The mixture was filtered through Celite and evaporated, providing 1.8 g of the product, in 89% yield; 1H NMR (DMSO-d6) δ 1.78-1.83 (m, 4H), 2.58-2.63 (m, 4H), 2.86 (t, J=6.0 Hz, 2H), 3.53 (by, 2H), 3.81 (s, 3H), 4.04 (t, J=6.0 Hz, 2H), 6.35 (dd, J=8.4 Hz, J=2.7 Hz, 1H), 6.49 (d, J=2.7 Hz, 1H), 6.61 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-f910474097f44e7f839977fa4e308a49
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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