1-[3-(2-Methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidine → HCID 17989386, compound

HRID 601504Notes

Reaction equation

HRID 601504 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]#[C:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 574214681-[3-(2-Methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidine

Product 1

HCID 17989386HCID 17989386, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 1-[3-(2-methoxy-4-nitro-phenyl)-prop-2-ynyl]-pyrrolidine (292 mg, 1.12 mmol) in EtOH (5 mL) and treat with 5% Pd/C. Purge the black mixture with hydrogen, then stir overnight at room temperature under a hydrogen atmosphere (1 atm). Filter the black mixture through a pad of Celite® and wash the solids with additional EtOH (20 mL). Concentrate the filtrate to give the title compound as an oil (240 mg, 91%). MS (ES+) 235.2 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 6.88 (d, 1H, J=8.3 Hz), 6.22-6.18 (m, 2H), 3.73 (s, 3H), 3.55 (s, 2H), 2.53-2.41 (m, 8H), 1.79-1.72 (m, 6H).

Workup

  1. customPurge the black mixture with hydrogen
  2. filtrationFilter the black mixture through a pad of Celite®
  3. washwash the solids with additional EtOH (20 mL)
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-8627b60a21ed47688acc81215a2f9d53
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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