Aluminium lithium hydride → 4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzylamine

HRID 586079노트

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HRID 586079 반응식
[CH:1]12[N:8]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3[C:17]([F:20])([F:19])[F:18])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:5]12[N:8]([C:9]3[CH:16]=[CH:15][C:12]([CH2:13][NH2:14])=[CH:11][C:10]=3[C:17]([F:20])([F:18])[F:19])[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 223376664-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile

생성물 1

HCID 223376164-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzylamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

4-(8-Azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile in THF (50 mL) was treated with solid LAH (0.68 g, 18 mmol) at 0° C. portionwise. The mixture was heated at reflux 1 hour, allowed to cool to 0° C., and quenched by addition of (Na2SO4 10H2O). The mixture was stirred 30 minutes, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 5% to 10% MeOH/CH2Cl2 to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.57 (d, 1H, J=2.0 Hz), 7.42 (dd, 1H, J=8.1, 2.0 Hz), 7.08 (d, 1H, J=8.4 Hz), 3.658 (m, 4H), 2.15 (bs, 2H), 1.92 (m, 2H), 1.88-1.55 (m, 5H), 1.48 (m, 3H); MS (ESI) 268 (M−NH2)+.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux 1 hour
  3. customquenched by addition of (Na2SO4 10H2O)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 5% to 10% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-ce5143269b854e60a9447a4fb40137bf
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933311B2

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