Trimethylsilyl cyanide → HCID 15176140, 화합물

HRID 2165532

반응식

HRID 2165532 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 15176140HCID 15176140, 화합물

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-3216517382fb49deaa2acd4da1c4f945
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940703

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