HCID 58980862, compound → 1-[2-(4-Amino-2-methoxyphenoxy)ethyl]pyrrolidin-3-ol

HRID 1181380Notes

Reaction equation

HRID 1181380 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:4]=1[O:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1>CCOC(C)=O.[Pd]>[NH2:18][C:16]1[CH:15]=[CH:14][C:4]([O:5][CH2:6][CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[C:3]([O:2][CH3:1])[CH:17]=1

Participants

4

Reactant 1

HCID 58980862HCID 58980862, compound

Product 1

HCID 589807751-[2-(4-Amino-2-methoxyphenoxy)ethyl]pyrrolidin-3-olYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidin-3-ol (0.169 g, 0.583 mmol) was taken up in EtOAc (5 mL) and 10% Pd/C (0.016 g) was added. The hydrogen gas was bubbled through the reaction and the reaction then placed under a hydrogen blanket. Stirred over night. Filtered through celite and concentrated to give 0.118 g (0.470 mmol, 81%) of the desired product. 1H NMR (CDCl3) δ 6.74 (d, 1H, J=8.5 Hz), 6.28 (s, 1H), 6.19 (d, 1H, J=8.5 hz), 4.34 (m, 1H), 4.05 (t, 2H, J=6.2 Hz), 3.79 (s, 3H), 3.03-2.83 (m, 5H), 2.63-2.59 (m, 1H), 2.42-2.38 (m, 1H), 2.23-2.14 (m, 1H), 1.75 (m, 1H).

Workup

  1. customThe hydrogen gas was bubbled through the reaction
  2. customthe reaction
  3. filtrationFiltered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0425d4e966a84f73a9b765b7cd0c9ffb
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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