4-(2-Benzyloxycarbonylamino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester → 4-(2-Amino-3-methyl-butyryl)-3-phenoxy-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]2[N:20]([C:23](=[O:39])[CH:24]([NH:28]C(OCC3C=CC=CC=3)=O)[CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:10]2[N:20]([C:23](=[O:39])[CH:24]([NH2:28])[CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:22][CH:9]12)=[O:7])([CH3:3])([CH3:2])[CH3:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A 500 mL Parr bottle was charged with crude 14 (410 mg, 0.76 mmol) and 10% Pd-on-carbon (50 mg) in reagent grade MeOH (10 mL). The mixture was pressurized to 50 PSI H2 then shaken for 2 h. The catalyst was removed by filtration through Celite® and the solids were washed with MeOH and EtOAc. The filtrate was concentrated in vacuo to afford 307 mg (quant.) of 15 which was used without further purification.