1-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline → 1-[(3-Pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline

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Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH2:13][CH:12]3[N:14]([C:15]([N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][CH2:19][CH2:18]4)=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH:8]=2)[CH:2]=1>C(O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:13][CH:12]3[N:14]([C:15]([N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH2:20][CH2:19][CH2:18]4)=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

In a high-pressure reactor, under nitrogen, 0.148 g of 5% palladium-on-charcoal is added to 0.240 g of 1-[(3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-2-en-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline solubilized in 9 ml of ethanol. The reaction mixture is placed under a hydrogen pressure of 3 atmospheres, at 25° C., and mechanically stirred for 15 hours. The palladium is filtered off on Whatman paper and washed with methanol. The solvent is evaporated off, and the residue then chromatographed on silica gel with an eluent gradient of heptane/ethyl acetate (3/7) to heptane/ethyl acetate (2/8). 0.146 g of 1-[(3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-8-yl)carbonyl]-1,2,3,4-tetrahydroquinoline is obtained.

Aufarbeitung

filtrationThe palladium is filtered off on Whatman paper
washwashed with methanol
customThe solvent is evaporated off
customthe residue then chromatographed on silica gel with an eluent gradient of heptane/ethyl acetate (3/7) to heptane/ethyl acetate (2/8)

Quellen und Nachweise

ORD-Eintrag: ord-39ab8fd4fca14bb9ab6afb54b16e7abe
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07897773B2

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