HCID 69621549, compound → HCID 69621483, compound

Participants

Reaction Steps

10% Pd/C catalyst (0.22 g) was added to a solution of the substrate 128 (0.95 g, 2.1 mmol) in absolute EtOH (200 mL). The reaction mixture was hydrogenated under pressure using a Parr hydrogenator at 55 psi H2 for 18 h. The reaction mixture was filtered through celite, and the celite washed with hot EtOH, taking care not to allow the filtration pad to dry out. Removal of excess solvent afforded the product as a colourless glass (0.84 g, 1.9 mmol, 92%); 1H NMR (270 MHz, CDCl3) δ 0.07 (s, 9H), 0.91-0.97 (m, 2H), 2.07-2.20 (m, 4H), 3.52-3.75 (m, 2H), 3.98-4.26 (m, 9H), 5.65 (d, 1H, J=9.71 Hz), 6.26 (br s, 1H), 7.14 (s, 1H); 13C NMR (CDCl3) δ 167.0, 157.3, 146.8, 143.4, 141.3, 124.9, 123.5, 105.5, 105.2, 85.8, 64.8, 64.6, 64.5, 61.2, 60.0, 56.4, 46.4, 28.9, 28.7, 23.1, 23.0, 17.3, −1.3, −1.5, −1.7.

Provenance & Evidence