Nicotine → (S)-trans-1-dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-1-pyridinium bromide

HRID 9789

反応式

HRID 9789 の反応式
[N:1]1[CH:6]=[C:5]([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(O)=O>[Br-:13].[CH2:14]([N+:1]1[CH:2]=[CH:3][CH:4]=[C:5]([C@@H:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:6]=1)[CH2:15][CH2:16]/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

4

反応物 2

HCID 89594NicotineHCID 11160306trans-1-Bromo-dec-4-ene

生成物 1

HCID 10249266(S)-trans-1-dec-4-enyl-3-(1-methyl-pyrrolidin-2-yl)-1-pyridinium bromide収率 74.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of (S)-nicotine (0.47 g, 2.9 mmol) in AcOH (15 ml) was added trans-1-bromo-dec-4-ene (1.55 g, 7.08 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 0.82 g (74%) of (S)-trans-1-dec-4-enyl-3-(1-methyl-pyrrolidin -2-yl)-1-pyridinium bromide (NDNB-4t) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.71 (1H, d, J=5.7 Hz), 9.07 (1H, s), 8.40 (1H, d, J=8.1 Hz), 8.08 (1H, dd, J=8.1, 6.0 Hz), 5.42 (2H, m), 5.00 (2H, t, J=6.9 Hz), 3.54 (1H, t, J=8.4 Hz), 3.25 (1H, m), 2.44 (2H, m), 2.25 (3H, s), 1.65–2.20 (8H, m), 1.66 (1H, m), 1.15–1.40 (6H, m), 0.87 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 146.50, 144.36, 143.79, 143.13, 128.52, 127.15, 67.05, 61.49, 56.86, 40.70, 36.07, 32.67, 31.76, 31.56, 29.27, 29.07, 23.39, 22.70, 14.27; Anal. Calcd for C20H33BrN2.0.3H2O: C, 62.10; H, 8.76; N, 7.24. Found: C, 62.03; H, 8.88; N, 7.12.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 days
  3. customAcOH was evaporated
  4. dissolutionthe residue was dissolved in CHCl3
  5. washThe mixture was washed with saturated aqueous NaHCO3, water and brine successively
  6. customdried
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-3e9bf89dccf542e48fad94bcad548578
出典データセット
uspto-grants-2006_08
特許番号
US07091357B2

関連ノート

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