[(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester → [(R)-1-((R)-Pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 1929779Notes

Reaction equation

HRID 1929779 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:27])[NH:14][C@@H:15]2[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16]2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:28])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:27])[NH:14][C@@H:15]2[CH2:19][CH2:18][NH:17][CH2:16]2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67022985[(R)-1-((R)-1-Benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 58024990[(R)-1-((R)-Pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of [(R)-1-((R)-1-benzyl-pyrrolidin-3-ylcarbamoyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester in ethanol under an inert atmosphere of argon is added palladium hydroxide on carbon. The reaction mixture is purged with nitrogen and placed under an atmosphere of hydrogen overnight. The mixture is filtered and the catalyst washed with ethanol. The organic portions are combined and concentrated in vacuo. The resulting brown oil is purified by column chromatography (Isolute™ Si, 2% MeOH in DCM) yield the title compound. MS (ES+) m/e 389.25 (MH+).

Workup

  1. customThe reaction mixture is purged with nitrogen
  2. filtrationThe mixture is filtered
  3. washthe catalyst washed with ethanol
  4. concentrationconcentrated in vacuo
  5. customThe resulting brown oil is purified by column chromatography (Isolute™ Si, 2% MeOH in DCM)

Sources & evidence

ORD record
ord-452736fb8eeb400e87a7116b7ce79684
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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