Diethyl 1,4-dihydro-4-(3-benzyloxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate → Diethyl 1,4-dihydro-4-(3-hydroxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate
Reaction equation
C([O:8][C:9]1[C:10]([CH:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH3:26])[NH:18][C:17]([CH3:27])=[C:16]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:11][CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[C:10]([CH:15]2[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:17]([CH3:27])[NH:18][C:19]([CH3:26])=[C:20]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11][CH:12]=[CH:13][CH:14]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Diethyl 1,4-dihydro-4-(3-benzyloxypyridyl)-2,6-dimethyl-3,5-pyridine dicarboxylate (7.0 grams; 0.016 mole) was hydrogenated in three batches using 1.2 grams of 10% Palladium on carbon. Material was dissolved in 300 ml ethanol and over a period of two hours there was a drop of 44 psi. The reaction mixtures were vacuum filtered through celite and the filtrate concentrated to approximately half the volume. Crystals formed on standing were filtered and collected. Recrystallization from acetonitrile yielded 6.2 grams of yellow crystals, m.p. 238°-239° C.