HCID 90391163, compound → HCID 90391033, compound

Participants

Reaction Steps

To a solution of 5-(hydroxymethyl)-14-hydroxycodeinone 4 (0.13 g, 0.379 mmol) in 5 mL of 1:1 ethanol-glacial acetic acid Pd/C (10%, 15 mg) was added. The mixture was evacuated and filled with H2 gas in a hydrogenation flask and maintained under 40 psi H2 pressure for 4 h. The reaction mixture was filtered through celite, the solvent was evaporated and the residue was basified with aqueous ammonia prior to CHCl3 extraction. Organic phases were combined, washed with brine, dried over anhydrous Na2SO4 and the solvent was evaporated. The residue was subjected to column chromatography (7:93 methanol-dichloromethane) to give the pure olefin reduced compound 5 as white foam (0.0915 g, 70%). 1H NMR (CDCl3, 400 MHz): δ 6.7 d (1H, J=8.6 Hz), 6.65 d (1H, J=8.6 Hz), 4.16 d (1H, J=10.9 Hz), 4.01 d (1H, J=11.7 Hz), 3.86 s (3H), 3.16 d (1H, J=18.7 Hz), 3.07 td (1H, J=5.4, 14.8 Hz), 2.96 d (1H, J=5.4 Hz), 2.67-2.51 m (2H), 2.43 s (3H), 2.40-2.29 m (2H), 2.25-2.15 m (1H), 1.96-1.87 m (1H), 1.74-1.63 m (1H), 1.47 d (1H, J=12.5 Hz). 13C NMR (CDCl3, 100 MHz): δ 210.47, 144.17, 142.88, 129.60, 124.43, 119.64, 114.49, 96.26, 70.29, 64.20, 61.74, 56.53, 50.58, 44.67, 42.65, 37.31, 31.21, 26.88, 21.91. MS (ESI): m/z 346.1 (M+1)+.

Provenance & Evidence