{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
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
Product 1
Reagents, catalysts & solvents 2
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.