3-[3-((R)-1-benzyl-pyrrolidin-3-yl)-ureido]-benzenesulfonamide → 3-((R)-3-pyrrolidin-3-ylureido)-benzenesulfonamide

HRID 2382374Notes

Reaction equation

HRID 2382374 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:26])[NH:15][C:16]2[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=2)[CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:26])[NH:15][C:16]2[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 666311133-[3-((R)-1-benzyl-pyrrolidin-3-yl)-ureido]-benzenesulfonamide

Product 1

HCID 666298133-((R)-3-pyrrolidin-3-ylureido)-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[3-((R)-1-benzyl-pyrrolidin-3-yl)-ureido]-benzenesulfonamide (25 g, 0.067 mol) in ethanol (250 mL) is purged with nitrogen, and palladium hydroxide (2.5 g, 20% w/w) is added. The suspension is purged with hydrogen and stirred under a positive pressure of hydrogen for 24 hours. Filtration though Celite® (filter material) and removal of solvent under reduced pressure gives the product as a colourless waxy solid.

Workup

  1. additionis added
  2. customThe suspension is purged with hydrogen
  3. filtrationFiltration
  4. filtrationthough Celite® (filter material) and removal of solvent under reduced pressure
  5. customgives the product as a colourless waxy solid

Sources & evidence

ORD record
ord-9ac68d1bf6214c45b6eaa277ed7e650c
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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