Sodium Methoxide → HCID 67001978, compound

Participants

Reaction Steps

Platinum(IV) oxide (35 mg, 0.154 mmol) was added to a solution of the product of Example 51A (1.20 g, 2.92 mmol) in methanol (150 mL), and the suspension was stirred under hydrogen (1 atm) for 1 hour. The reaction flask was evacuated and purged with nitrogen (4 cycles), and the mixture was filtered through a pad of diatomaceous earth with a methanol (30 mL) rinse. A solution of 25% sodium methoxide in methanol (Aldrich, 1.83 g, 8.47 mmol) was added to the filtrate, and the solution was stirred at reflux under nitrogen for 41 hours and then cooled to room temperature. The reaction mixture was concentrated under vacuum, and the residue was purified by chromatography (SiO2, eluted with CH2Cl2—CH3OH, 95:5), followed by crystallization from ethanol (2 mL) to provide the title compound: 1H NMR (300 MHz, CD3OD) δ ppm 2.15 (dd, J=13.7, 3.0 Hz, 1H), 2.22-2.32 (m, 1H), 2.31 (t, J=10.7 Hz, 1H), 2.75 (dd, J=13.7, 6.5 Hz, 1H), 2.83-2.96 (m, 2H), 3.23 (td, J=12.7, 2.8 Hz, 1H), 3.51-3.59 (m, 1H), 3.60 (s, 2H), 3.64-3.74 (m, 1H), 6.99 (dd, J=7.7, 5.0 Hz, 1H), 7.22-7.40 (m, 6H), 8.08 (dd, J=4.8, 1.6 Hz, 1H); MS (DCI) m/z 309 (M+H)+.

Provenance & Evidence