反应 #9895

反应方程式

(S)-nicotine

11-bromo-undec-1-ene

→

(S)-3-(1-methyl-pyrrolidin-2-yl)-1-undec-10-enyl-pyridinium bromide

收率 67.0%

溶剂

AcOH

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux for 3 days
3. 3
   其他AcOH was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   洗涤The mixture was washed with saturated aqueous NaHCO3, water and brine successively
6. 6
   其他dried
7. 7
   其他Evaporation of the solvent

实验过程

To a stirred solution of (S)-nicotine (0.14 g, 0.86 mmol) in AcOH (4 ml) was added 11-bromo-undec-1-ene (0.50 g, 2.1 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3. The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried. Evaporation of the solvent followed by titration with ether afforded 0.22 g (67%) of (S)-3-(1-methyl-pyrrolidin-2-yl)-1-undec-10-enyl-pyridinium bromide (NUNB-10e) as a brown oil. 1H NMR (300 Mz, CDCl3) δ 9.61 (1H, d, J=5.7 Hz), 9.22 (1H, s), 8.40 (1H, d, J=8.1 Hz), 8.08 (1H, dd, J=8.1, 6.0 Hz), 5.77 (1H, m), 4.85–5.10 (4H, m), 3.54 (1H, t, J=8.1 Hz), 3.24 (1H, m), 2.43 (2H, m), 2.23 (3H, s), 1.80–2.15 (6H, m), 1.63 (1H, m), 1.10–1.44 (12H, m); 13C NMR (75 MHz, CDCl3) δ 146.43, 144.21, 143.65, 143.09, 139.05, 128.44, 114.16, 66.97, 62.02, 56.82, 40.62, 35.99, 33.88, 32.24, 29.44×2, 29.18×2, 28.98, 29.26, 23.33.

来源