Methanol → HCID 10684223, compound

Participants

Reaction Steps

A mixture of compound 14 (440 mg, 1.01 mmol), dry methanol (10 mL) and disodium hydrogen phosphate (574 mg, 4.04 mmol) was stirred under nitrogen at room temperature. To this mixture was added 6.20 g of 6% Na-Hg in three portions and the reaction was heated at ref lux for 2 h. After cooling, water (200 mL) was added and the mixture was extracted with ether (3×200 mL). The ether layers were combined, dried (MgSO4), filtered (Celite), and evaporated to give an oil that solidified under vacuum. After rotary chromatography 142 mg (50%) of compound 15 was obtained as an oil. The oil quickly darkened on exposure to air and was used immediately for the next step. A small portion of the oil was treated with ethereal HCl and the hydrochloride salt of compound 15 was recrystallized from ethanol-ether: mp (HCl salt) 190° C. (dec); 1H NMR (CDCl3, base) δ 3.13 (dd, 1 H, J=10.8, 12 Hz, H-1a), 3.50 (dd, 1 H, J=3.4, 17.4 Hz, H-1b), 3.70 (m, 1 H, H-11b), 3.839 (s, 3 H, OCH3), 3.842 (s, 3 H, OCH3), 4.03 (dd, 1 H, J=6, 12 Hz, H-7a), 4.08 (s, 2 H, H-3), 4.33 (d, 1 H, J=17.4 Hz, H-7b), 6.78 (d, 1 H, J=8.24 Hz, ArH), 6.92 (m, 3 H, ArH), 7.11 (t, 1 H, J=7.5 Hz, ArH), 7.18 (d, 1 H, J=7.5 Hz, ArH); MS (CI) m/z 282 (100); HRCIMS Calculated for C18H19NO2: 282.1494; Found 282.1497.

Provenance & Evidence