Acetic Acid → 1-(1,1-Dimethylethyl) 4-[(2-methylphenyl)methyl]-1,4-piperidinedicarboxylate

Reaktionsgleichung

C([O:8][C:9](=[O:31])[C:10]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)C1C=CC=CC=1.C(O)(=O)C>[Pd].CO>[C:19]([O:18][C:16]([N:13]1[CH2:12][CH2:11][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])([C:9]([OH:31])=[O:8])[CH2:15][CH2:14]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Komponenten

Versuchsvorschrift

A mixture of 4-(2-methylbenzyl) N-t-butoxycarbonyl isonipecotic acid benzyl ester (2.36 g, 5.57 mmol), 5% Palladium on charcoal catalyst (250 mg), and glacial acetic acid (3 ml) in methanol (75 ml), was hydrogenated at 51 p.s.i. overnight, in a Parr shaker. The reaction mixture was then filtered through a pad of Celite and the pad washed several times with methanol. The combined filtrates were then concentrated in vacuo to the product, a white solid. 30 mg of this material was recrystallized from toluene to afford fine white crystals m.p. 176°-179° C. dec.