1-(2-nitrobenzyl)pyrrolidine → HCID 89314201, compound

HRID 239200Notes

Reaction equation

HRID 239200 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)([O-])=[O:2]>CN1CCOCC1.[Pt]>[CH2:9]1[CH2:8][N:7]([CH2:6][C:5]2[C:4]([NH:1][OH:2])=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 2643101-(2-nitrobenzyl)pyrrolidine

Product 1

HCID 89314201HCID 89314201, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 79724-MethylmorpholineSolvent

Procedure

The N-(2-nitrobenzyl)-pyrrolidine (20 mmol) was dissolved in N-methyl-morpholine (20 ml). Platinum on carbon (5 mol-%, 0.17 mmol, 350 mg, Degussa Type F105 RS/W) was added. The reaction vessel was evacuated and flushed with nitrogen three times, before a hydrogen atmosphere was applied. Thin layer chromatography control showed complete consumption of the starting material after 4 hours. The platinum catalyst was removed by filtration over celite. The crude product was obtained after evaporation of all volatiles under reduced pressure in a purity of >90%, as measured by 1H NMR.

Workup

  1. customThe reaction vessel was evacuated
  2. customflushed with nitrogen three times, before a hydrogen atmosphere
  3. customconsumption of the starting material after 4 hours
  4. customThe platinum catalyst was removed by filtration over celite

Sources & evidence

ORD record
ord-cc5da4cdbb4c45e2b4367a256315a325
Source dataset
uspto-grants-2014_02
Patent number
US08642780B2

Reaction notes

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