HCID 67367212, compound → HCID 67365517, compound

HRID 2189235Notes

Reaction equation

HRID 2189235 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([N+:13]([O-])=O)[C@H:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[H][H].[Ni]>[NH3:8].[CH2:1]([N:8]1[CH2:9][C@@H:10]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C@H:11]([NH2:13])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 67367212HCID 67367212, compound

Product 2

HCID 222AmmoniaHCID 67365517HCID 67365517, compoundYield 124.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

trans-1-Benzyl-3-(4-methoxyphenyl)-4-nitropyrrolidine (0.205 g, 0.66 mmol) was dissolved in methanol (10 mL) and hydrogenated under a hydrogen atmosphere at atmospheric pressure in the presence of Raney nickel (˜8 mL). After stirring for 2 h the solution was concentrated in vacuo and purified by ion exchange chromatography on SCX-2 (solute acidic resin (2 g), eluting with methanol and then 1 M ammonia in methanol to give the title compound (0.116 g, 62%) as a colourless oil that was used without further purification.

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified by ion exchange chromatography on SCX-2 (solute acidic resin (2 g)
  3. washeluting with methanol

Sources & evidence

ORD record
ord-c766404aeba441acabed37ed48102abe
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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