3-(benzyloxy)-N-cyclobutyl-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide → N-cyclobutyl-3-hydroxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide
Reaction equation
[CH:1]1([NH:5][C:6]([C:8]2[N:9]([CH3:24])[C:10]([CH3:23])=[CH:11][C:12](=[O:22])[C:13]=2[O:14]CC2C=CC=CC=2)=[O:7])[CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([NH:5][C:6]([C:8]2[N:9]([CH3:24])[C:10]([CH3:23])=[CH:11][C:12](=[O:22])[C:13]=2[OH:14])=[O:7])[CH2:2][CH2:3][CH2:4]1Participants
4
Procedure
A mixture of N-cyclobutyl-3-benzyloxy-1,6-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxamide (1.528 g, 4.68 mmol, 1.0 equiv), 10% Pd on activated carbon (200 mg, wet), and ethanol (200 ml) was stirred under 50 psi of H2 at room temperature for 2.5 h. The catalyst was filtered through Celite and the filtrate was evaporated to give a solid, which was recrystallized from MeOH gave the titled compound (0.57 g, 51.5%) as a white solid.