HCID 612931, compound → HCID 69223603, compound

HRID 30229Notes

Reaction equation

HRID 30229 reaction equation
[C:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CO.[Pd]>[C:1]([N:8]1[CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][CH:9]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 612931HCID 612931, compound

Product 1

HCID 69223603HCID 69223603, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-Boc-2,5-diphenylpyrrole (1.027 g, 3.22 mmol) in methanol (80 ml) was added palladium (5%) on activated carbon (0.250 g). The reaction mixture was hydrogenated (10 psi) for 1.5 hours. Filtration and evaporation to dryness afforded N-Boc-2,5-diphenylpyrrolidine (1.01 g, 97%). 1H-NMR (CDCl3): δ ppm 7.20-7.60 (m, ArH, 10H), 5.0 (in, ArCH, 2H), 2.45 (m, CH2, 2H), 1.17 (s, CH3, 9H)

Workup

  1. customfor 1.5 hours
  2. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-5ccfbe18e34c4c84bcced83c010d36d2
Source dataset
uspto-grants-2008_09
Patent number
US07423059B2

Reaction notes

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