HCID 54162185, compound → HCID 54370100, compound

HRID 2230122Notes

Reaction equation

HRID 2230122 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[O:7][C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=1[O:17][CH3:18]>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[O:7][C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:9]=1[O:17][CH3:18]

Participants

4

Reactant 1

HCID 54162185HCID 54162185, compound

Product 1

HCID 54370100HCID 54370100, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (S)-1-methyl-2-(2-methoxy-5-nitrophenoxy)pyrrolidine (D43) (6.79 g; 0.0255 mol) in ethanol (200 ml) was hydrogenated in the presence of 5% Pd/C catalyst (0.5 g added as an aqueous slurry) at atmospheric pressure and RT for 16 hours. The catalyst was removed by filtration through kieselguhr and the filtrate evaporated in vacuo to yield the title compound (D44) (5.64 g; 93%) MH+=237.

Workup

  1. additionadded as an aqueous slurry) at atmospheric pressure and RT for 16 hours
  2. customThe catalyst was removed by filtration through kieselguhr
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-537d781cafb746bda675724a0b4b8138
Source dataset
uspto-grants-2002_07
Patent number
US06423717B1

Reaction notes

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