HCID 10440854, compound → HCID 15816444, compound

Participants

Reaction Steps

10% Pd-C (227 mg) was added to a solution of (12) (0.346 g, 0.372 mmol) in MeOH (100 mL). The reaction flask was degassed three times with nitrogen and hydrogen gas was introduced at 1 atm. The mixture was rapidly stirred at room temperature for 20 minutes. After the reaction flask was evacuated and filled with nitrogen several times, the catalyst was filtered through a sintered glass filter (10-15μ) and solids were washed with MeOH. After solvent removal by rotary evaporation, the residue was passed through a short Sephadex LH-20 column, eluting with MeOH. The band was dried to provide 199 mg (81%) of (13) as an amorphous white solid: 300 MHz NMR (d6 -DMSO) δ 1.12-1.53 (m+s, 27 H), 1.95 (s, 3 H), 2.25 (t, 4 H, J=7), 2.52-2.60 (m, 4 H), 2.82-3.03 (m, 6 H), 3.43 (t, 6 H, J=6), 7.4 (m, 1 H), 7.8 (m, 2 H), 9.7 (br s, 3 H). The spectrum was identical to an authentic sample of (13).

Provenance & Evidence