Lithium Chloride → cis-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetonitrile
Reaktionsgleichung
C(OC(=O)[CH:5]([C:23]#[N:24])[C:6]1[S:7][CH:8]=[C:9]([C:11]([N:13]2[C@@H:22]3[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:10]=1)C.[Cl-].[Li+]>CS(C)=O.C(Cl)Cl>[N:13]1([C:11]([C:9]2[CH:10]=[C:6]([CH2:5][C:23]#[N:24])[S:7][CH:8]=2)=[O:12])[C@@H:22]2[C@@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][CH2:14]1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester (0.168 g, 0.46 mmol) and lithium chloride (0.5 mmol) were dissolved in DMSO (5 mL) and heated to 160° C. by microwave irradiation for one minute. The solution was diluted with DCM (10 mL) and washed with water. The resulting organic solution was dried and the solvent evaporated to give an oil which was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.025 g). LCMS m/z 289.25 [M+H]+ RT=10.02 min (Analytical Method 2).
Aufarbeitung
- washwashed with water
- customThe resulting organic solution was dried
- customthe solvent evaporated
- customto give an oil which
- customwas purified by HPLC
- washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
- additionThe fractions containing the desired product
- concentrationwere concentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-24a3398ea6a74b27a0e159e900b36397
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08362008B2
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