Trimethylsilyl cyanide → HCID 15176140、化合物

HRID 2165532ノート

反応式

HRID 2165532 の反応式
C[Si]([C:5]#[N:6])(C)C.[N:7]12[CH2:15][CH:11]([CH2:12][CH2:13][CH2:14]1)[C:10](=[O:16])[CH2:9][CH2:8]2>ClCCl.[I-].[Zn+2].[I-]>[NH2:6][CH2:5][C:10]1([OH:16])[CH:11]2[CH2:15][N:7]([CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:9]1

参加物

5

反応物 2

HCID 82115Trimethylsilyl cyanideHCID 4178971-Azabicyclo(3.3.1)nonan-4-one

生成物 1

HCID 15176140HCID 15176140、化合物

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Trimethylsilyl cyanide (3 ml) was added dropwise to a stirred solution of 1-azabicyclo[3.3.1]nonan-4-one (2.5 g) and zinc iodide (0.15 g) in dry dichloromethane (20 ml) and the resulting mixture was heated at reflux for 4 hours. The mixture was cooled and the solvent removed at reduced pressure; the residue was dissolved in dry tetrahydrofuran (20 ml) and cooled to 0° C. A solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added and the resulting solution stirred overnight at room temperature. Water (0.7 ml), followed by 15% sodium hydroxide (aq) (0.7 ml) and water (2.1 ml) were then added and the precipitate removed by filtration. Evaporation of the filtrate yielded the title compound (2.2 g); δH (360 MHz, CDCl3) 1.2-1.3 (2H, m, CH2), 1.34 (1H, m, CHH), 1.41 (1H, m, CHH), 1.6 (2H, m, CH2), 1.7-1.74 (1H, m, CHH), 1.76-1.91 (2H, m, CH2), 2.11-2.16 (1H, m, CHH), 2.67-3.18 (8H, m); m/z 170 (M+).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent removed at reduced pressure
  5. dissolutionthe residue was dissolved in dry tetrahydrofuran (20 ml)
  6. additionA solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added
  7. additionwere then added
  8. customthe precipitate removed by filtration
  9. customEvaporation of the filtrate

出典と根拠

ORDレコード
ord-3216517382fb49deaa2acd4da1c4f945
出典データセット
uspto-grants-1990_07
特許番号
US04940703

反応ノート

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