Sodium Bicarbonate → HCID 46832153, compound

Participants

Reaction Steps

12-epi-Salvinorin A (52 mg, 0.12 mmol) was dissolved in THF (3 mL) and H2O (3 mL). To this solution was added NaHCO3 (202 mg, 2.4 mmol), and the reaction was stirred at rt for two hours. The mixture was then diluted with EtOAc, washed with brine, and dried over MgSO4. After evaporation of the solvent, flash chromatography (0% to 5% MeOH in hexanes) gave alcohol 35 as an off-white solid. (27 mg, 58% yield); Rf 0.16 (98:2, CH2Cl2/MeOH); 1H NMR (300 MHz, CDCl3) δ 7.43 (m, 1H), 7.41 (t, J=1.6, 1H), 6.41 (m, 1H), 5.30 (dd, J=6.1, 11.5, 1H), 4.21-3.97 (m, 1H), 3.72 (s, 3H), 2.73 (dd, J=3.1, 13.5, 1H), 2.53-2.41 (m, 3H), 2.34 (dd, J=11.6, 14.6, 1H), 2.18-1.93 (2H), 1.92-1.69 (m, 4H), 1.63 (m, 1H), 1.39 (s, 3H), 1.04 (s, 3H).

Provenance & Evidence