[Synthesis]
General procedure for the synthesis of 4-(3-pyridinyl)-1-butyn-1-ol from 4-(3-pyridinyl)-3-butyn-1-ol: 4-(3-pyridinyl)-3-butyn-1-ol (0.32 g, 2.2 mmol) was dissolved in EtOH (44 mL) and passed through a H-Cube?flow hydrogenation reactor fitted with 10% Pd/C catalyst to carry out the hydrogenation reaction (flow rate : 1.0 mL/min; pressure: 1.0 bar; temperature: 3.5°C). After completion of the reaction, the output solution was concentrated to dryness to give an oily residue (0.31 g). Purification by conventional silica gel fast chromatography (eluent: CH2Cl2/MeOH, 95:5) afforded pure 4-(3-pyridyl)-1-butanol (0.294 g, 89% yield) as a colorless liquid. rf = 1.16 mm. m/z MS (ESI) m/z: 152 [M-H]-. 1H NMR (DMSO-d6) δ: 8.43 (m. 1H), 8.38 (dd, 1H, J = 4.8, 1.5 Hz), 7.61 (dt, 1H, J = 7.8, 2.1 Hz), 7.30 (dd, 1H, J = 7.8, 4.8 Hz), 4.37 (t, 1H, J = 5.2 Hz), 3.41 (q, 2H, J = 5.2 Hz), 2.59 (t, 2H, J = 7.7 Hz), 1.64-1.55 (m, 2H), 1.47-1.38 (m, 2H). |
[References]
[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 6, p. 2573 - 2590
[2] Patent: WO2014/144836, 2014, A2. Location in patent: Paragraph 0614; 0615
[3] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 1077 - 1080 |