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

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Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-ce5143269b854e60a9447a4fb40137bf
Quelldatensatz: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06933311B2

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