Hydrochloric Acid → HCID 11258796, compound

Participants

Reaction Steps

The product of Example 39A (105 mg, 0.25 mmol) was treated with 1-phenyl-propan-1-one (Aldrich, 67 mg, 0.5 mmol) and HCl (Aldrich, 4 M in dioxane, 0.5 mL, 2 mmol) in EtOH (3.0 mL) at 80° C. for 10 h. The mixture was concentrated and the title compound was was purified by preparative HPLC (Xterra™, column, Xterra RP-18 5 μm, 30×100 mm. Eluting Solvent, MeCN/H2O (NH4HCO3, 0.1 M, pH=10) (v. 40/60 to 70/30 over 20 min.) Flow rate, 75 mL/min., uv, 250 nm) as solid (60 mg, yield, 57%). 1H NMR (300 MHz, CD3OD) δ 1.45–1.80 (m, 4H), 2.09–2.19 (m, 1H), 2.37 (s, 3H), 2.62–2.97 (m, 4H), 3.19–3.44 (m, 1H), 4.34–4.53 (m, 1H), 6.81 (dd, J=8.6, 2.2 Hz, 1H), 6.85–7.04 (m, 4H), 7.09 (d, J=2.4 Hz, 1H), 7.27–7.38 (m, 2H), 7.46 (t, J=7.6 Hz, 2H), 7.63 (d, J=7.1 Hz, 2H) ppm; MS (DCl/NH3) m/z 425 (M+H)+.

Provenance & Evidence