Acetic Acid → HCID 21969058, compound

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Reaction Steps

A mixture of (5R,6S)-3-(2-methoxy-5-trifluoromethoxyphenyl)-6-phenyl-1-oxa-7-aza-spiro[4.5]dec-3-ene (Example 2; 1.4 g), 10% palladium hydroxide/carbon (0.25 g) in methanol (90 ml) containing acetic acid (9 ml) was hydrogenated at 50 psi for 16 h. The solution was filtered, evaporated and the residue was crystallized twice from hexane to give the title compound. m.p. 91-104° C. 1H NMR (250 MHz, CDCl3) δ 7.50-7.54 (2H, m), 7.33-7.36 (3H, m),), 6.90 (1H, dd, J 8.9, 2.07 Hz), 6.68 (1H, d, J 8.9 Hz), 6.17 (1H, d, J 2.7 Hz), 4.08 (1H, t, J 7.8 Hz), 3.75 (1H, m), 3.69 (4H, s+d), 3.24 (1H, bd), 3.12 (1H, dd, J 10.3, 8.03 Hz), 2.82 (1H, td, J 12.4, 2.6 Hz), 2.16-1.80 (6H, m), and 1.55-1.64 (2H, m). m/z (ES+) 408 (M+1).

Provenance & Evidence