{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 1929776Notes

Reaction equation

HRID 1929776 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 overnight. 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-f95308dd2cca410bb12a91494637422d
Source dataset
uspto-grants-2012_05
Patent number
US08188100B2

Reaction notes

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