Acetic Acid → Methyl 3-hydroxyazetidine-3-carboxylate

Reaktionsgleichung

C([N:14]1[CH2:17][C:16]([OH:22])([C:18]([O:20][CH3:21])=[O:19])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[OH:22][C:16]1([C:18]([O:20][CH3:21])=[O:19])[CH2:17][NH:14][CH2:15]1

Komponenten

Versuchsvorschrift

A reactor was charged with methyl 1-benzhydryl-3-hydroxyazetidine-3-carboxylate (1.6 g, 5.4 mmol), 10% Pd/C (0.300 g, 2.8 mmol), and glacial acetic acid (0.300 mL, 5.2 mmol) in MeOH (30 mL). The mixture was allowed to stir for 3 h under 50 psig of H2. The crude was filtered through Celite and rinsed with MeOH. After evaporation, the solid was rinsed with Et2O to give methyl 3-hydroxyazetidine-3-carboxylate as the acetic acid salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.74 (d, J=9.1 Hz, 2H), 3.69 (s, 3H), 3.44 (d, J=8.9 Hz, 2H), 1.88 (s, 3H).