[Synthesis]
GENERAL STEPS: 4-(2-pyridyl)-3-butyn-1-ol (0.4 g, 2.72 mmol) was dissolved in ethanol (12 mL) to prepare a 0.23 M solution. The solution was passed through a hydrogenation reactor equipped with 10% Pd(OH)2 catalyst (flow rate: 1.0 mL/min; pressure: 1.0 bar; temperature: 25°C). Upon completion of the reaction, the effluent was concentrated to dryness to afford 4-(2-pyridyl)-1-butanol (0.36 g, 88% yield), and the product could be used in the subsequent steps without further purification. rf = 1.11 mm. mass spectra (ESI) m/z: 152 [M+H]+, 174 [M+Na]+. 1H NMR (DMSO-d6) δ: 8.49-8.43 (m, 2H), 7.68 (td, 1H, J = 7.6, 1.9 Hz), 7.23 (d, 1H, J = 7.6 Hz), 7.18 (ddd, 1H, J = 7.6, 5.4, 1.9 Hz), 3.40 (t, 2H, J = 6.6 Hz), 2.71 (t, 2H, J = 6.6 Hz), 1.74-1.63 (m 2H), 1.50-1.39 (m, 2H). |
[References]
[1] European Journal of Organic Chemistry, 2011, # 2, p. 271 - 279
[2] Patent: WO2014/144836, 2014, A2. Location in patent: Paragraph 0528; 0529
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080 |