반응 #9882

반응 방정식

(S)-nicotine

trans-1-bromo-oct-3-ene

→

(S)-trans-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridinium bromide hydrobromide salt

수율 62.5%

용매

AcOH

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 3 days
3. 3
   기타AcOH was evaporated
4. 4
   기타the residue was recrystallized in ethyl acetate-CHCl3

실험 절차

To a stirred solution of (S)-nicotine (0.46 g, 2.8 mmol) in AcOH (10 ml) was added trans-1-bromo-oct-3-ene (1.37 g, 7.17 mmol). The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was recrystallized in ethyl acetate-CHCl3 to afford (S)-trans-3-(1-methyl-pyrrolidin-2-yl)-1-oct-3-enyl-pyridinium bromide hydrobromide salt (NONB-3t) (0.76 g, 62%) as hygroscopic white crystals: 1H NMR (300 MHz, CDCl3) δ 11.55 (1H, s), 10.27 (1H, s), 9.46 (1H, d, J=7.5 Hz), 9.16 (1H, d, J=5.7 Hz), 8.22 (1H, dd, J=7.5, 5.7 Hz), 5.72 (1H, m), 5.41 (2H, m), 4.88 (2H, m), 3.98 (1H, m), 3.38 (1H, m), 2.94 (3H, s), 2.60–2.90 (3H, m), 2.43 (3H, m), 1.86 (2H, m), 1.00–1.25 (4H, m), 0.79 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 147.29, 146.41, 145.11, 137.58, 134.31, 128.44, 122.37, 67.18, 62.27, 56.04, 38.57, 34.49, 32.30, 32.00, 31.41, 22.32, 21.83, 14.12; Anal. Calcd for C18H30Br2N2.0.3H2O: C, 49.22; H, 6.93; N, 6.38. Found: C, 49.25; H, 7.03; N, 6.30.

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