{4-[3-((R)-1-Benzyl-pyrrolidin-3-yl)-ureido]-cyclohexyl}-carbamic acid tert-butyl ester → [4-((R)-3-Pyrrolidin-3-ylureido)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 215872Notes

Reaction equation

HRID 215872 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([NH:17][C@@H:18]2[CH2:22][CH2:21][N:20](CC3C=CC=CC=3)[CH2:19]2)=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:30])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([NH:17][C@@H:18]2[CH2:22][CH2:21][NH:20][CH2:19]2)=[O:16])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67022947{4-[3-((R)-1-Benzyl-pyrrolidin-3-yl)-ureido]-cyclohexyl}-carbamic acid tert-butyl ester

Product 1

HCID 58025036[4-((R)-3-Pyrrolidin-3-ylureido)-cyclohexyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of {4-[3-((R)-1-Benzyl-pyrrolidin-3-yl)-ureido]-cyclohexyl}-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 argon and placed under an atmosphere of hydrogen for over night. The mixture is filtered and the catalyst washed with ethanol. The organic portions are combined and concentrated in vacuo to yield the title compound.

Workup

  1. customThe reaction mixture is purged with argon
  2. filtrationThe mixture is filtered
  3. washthe catalyst washed with ethanol
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a54a53c6fcf44a1295e36d51b740b374
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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