D-Psicose → Ethyl 3,5-dimethyl-4-oxo-1,4-dihydropyridine-2-carboxylate

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Reaction Steps

To a solution of pyridone 5 (5.1 g, 17.89 mmol) in acetic acid (100 ml) was added 10% Pd--C (0.2 g), and the reaction mixture was hydrogenated (55 Psi) at room temperature overnight. The mixture was then filtered through Celite and the filtrate was evaporated. The residue was thoroughly washed with 10% potassium carbonate, water and dried in vacuo to give compound 6 as a white powder (3.3 g, 95% yield) m.p. 124°-126° C. 1H-NMR (DMSO-d6) δ 7.52 (brs, 1H), 4.45 (q, J=7.2 Hz, 2H), 2.40 (s, 3H), 2.07 (s, 3H), 1.42(t, J=7.2 Hz, 3H). Ms(13eV)m/z(%): 195.0(M+, 100), 165.9(40), 148.9(50), 122.9(80), 121.0(100). Anal. Calcd for C10H13NO3 : C, 61.53; H, 6.71; N, 7.18. Found: C, 61.48; H, 6.63; N, 7.09.

Provenance & Evidence