Nicotine → (S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide

HRID 9817ノート

反応式

HRID 9817 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][C:16]#[C:17][CH2:18][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][C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

4

反応物 2

HCID 89594NicotineHCID 14534130HCID 14534130、化合物

生成物 1

HCID 10407342(S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide収率 51.8%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of (S)-nicotine (0.46 g, 2.8 mmol) in AcOH (15 ml) was added 1-bromo-dec-3-yne (1.50 g, 6.91 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 0.55 g (51%) of (S)-1-dec-3-ynyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NDNB-3y) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.77 (1H, d, J=5.7 Hz), 9.14 (1H, s), 8.43 (1H, d, J=8.1 Hz), 8.04 (1H, dd, J=8.1, 5.7 Hz), 5.16 (2H, m), 3.52 (1H, t, J=8.1 Hz), 3.27 (1H, m), 3.03 (2H, m), 2.47 (2H, m), 2.26 (3H, s), 1.85–2.10 (4H, m), 1.70 (1H, m), 1.15–1.45 (8H, m), 0.86 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 145.91, 144.24, 144.12, 143.57, 128.02, 86.16, 73.98, 67.24, 60.66, 56.87, 40.70, 36.05, 31.44, 28.86, 28.75, 23.36, 22.71, 22.45, 18.82, 14.27; Anal. Calcd for C20H31BrN2.0.7H2O: C, 61.28; H, 8.33; N, 7.15. Found: C, 61.14; H, 8.21; N, 7.14.

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-3fdcf2a8f87f46b7a88d01e0c4bc8690
出典データセット
uspto-grants-2006_08
特許番号
US07091357B2

反応ノート

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