HCID 68291108, compound → HCID 70557102, compound

HRID 2205916Notes

Reaction equation

HRID 2205916 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][C:14]=1[N+:15]([O-])=O)[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:12]=[CH:13][C:14]=1[NH2:15]

Participants

4

Reactant 1

HCID 68291108HCID 68291108, compound

Product 1

HCID 70557102HCID 70557102, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd on carbon (12 mg, 0.866 mmol) was added to a solution of 1-(3-methoxy-4-nitrobenzyl)pyrrolidine (Preparation 105, 180 mg, 0.76 mmol) in EtOH (3 mL). The reaction mixture was degassed and then stirred for 1 hour at room temperature under an atmosphere of hydrogen. The reaction was filtered on a pad of Celite and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel column chromatography eluting with 5% methanol in dichloromethane to afford the title compound as a colourless oil (0.12 g, 76.3%). 1H-NMR (500 MHz, CDCl3): δ 1.79 (t, J=6.7 Hz, 4H), 2.5 (t, J=6.7 Hz, 4H), 3.53 (s, 2H), 3.75 (s, br, 2H), 3.86 (s, 3H), 6.65 (d, J=9.3 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 6.81 (d, J=1.5 Hz, 1H).

Workup

  1. customThe reaction mixture was degassed
  2. filtrationThe reaction was filtered on a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified on silica gel column chromatography
  5. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7f992eaf43944908827b6e7e0af8ca99
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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