Ammonium formate → HCID 69655001, compound

Participants

Reaction Steps

Ammonium formate (0.57 g, 9.1 mmol) was added to a solution of N-acetyl-N-[4-(3-{benzyl-[(2S)-3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-amino}-azetidin-1-yl)-phenyl]-acetamide (which was obtained in Example 402) (0.25 g, 0.45 mmol) and 10% Pd/C (0.05 g) in dry methanol (7 mL). The reaction was stirred at room temperature overnight. The solution was passed through a pad of celite and then was concentrated. The crude solid was treated with saturated aqueous NaHCO3 (30 mL) followed by extraction with ethyl acetate (3×20 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and evaporated to afford 0.18 g of the desired product as a white solid; 1H NMR (300 MHz, CDCl3) δ 2.05 (s, 6H), 2.61 (s, 1H), 2.75 (m, 2H), 3.49 (m, 2H), 3.75 (m, 1H), 3.85 (d, 2H, J=7.13 Hz), 4.02 (t, 2H, J=5.3 Hz), 4.12 (q, 1H), 6.32 (d, 2H, J=11.12 Hz), 6.90 (d, 2H, J=11.32 Hz), 6.55 (q, 4H, J=4.6 Hz), 7.53 (d, 2H, J=7.02 Hz), 7.61 (brs, 1H); MS (ES) m/z: 414.0 (MH+).

Provenance & Evidence