3-Hex-1-ynyl-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine → 5-Hexenyl-3-(1-methyl-2-(s)-pyrrolidinylmethoxy)pyridine
反応式
[C:1]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH3:20])[CH:10]=[N:11][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH:1]([C:7]1[CH:8]=[C:9]([O:13][CH2:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH3:20])[CH:10]=[N:11][CH:12]=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]参加物
4
実験手順
To a solution of 5-(1-hexynyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (from Example 4a, 100 mg, 0.37 mmol) in MeOH (3.0 mL) was added Lindlar's catalyst (10 mg). The mixture was stirred at room temperature overnight. The solvent was removed, and the residue was chromatographed on a silica gel column, eluting with NH4OH/MeOHTEtOAc 0:1:9 and 1:10:90 to afford a light yellowish oil (98 mg, 98%). MS (CI/NH3) m/z 277 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ0.88 (t, J=4.8 Hz, 3H), 1.23-1.37 (m, 6H), 1.53-1.62 (m, 2H), 1.70-2.08 (m, 4H), 2.26-2.36 (m, 1H), 2.48 (s, 3H), 2.56 (t, J=7.7 Hz, 2H), 2.58-2.71 (m, 1H), 3.07-3.14 (m, 1H), 3.88-4.05 (m, 2H), 7.03 (dd, J=3.0 Hz, J=J=2.1 Hz, 1H), 8.06 (d, J=2.1 Hz, 1H), 8.13 (d, J=3.0 Hz, 1H).