Ethyl cyanoacetate → cis-Cyano-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-acetic acid ethyl ester
Reaktionsgleichung
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:10])[CH2:7][C:8]#[N:9])[CH3:4].Br[C:12]1[S:16][CH:15]=[C:14]([C:17]([N:19]2[CH:28]3[CH:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:13]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:5][C:6](=[O:10])[CH:7]([C:8]#[N:9])[C:12]1[S:16][CH:15]=[C:14]([C:17]([N:19]2[C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27]3)[CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:13]=1)[CH3:4]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
Sodium hydride (60% dispersion in mineral oil; 400 mg) was added to a solution of ethylcyanoacetate (0.450 g) in THF (10 mL) and the mixture stirred for 10 minutes. A solution of (5-bromo-thiophen-3-yl)-(octahydro-quinolin-1-yl)-methanone (0.326 g) and PdCl2(PPh3)2 (0.035 g) in THF (2 mL) was then added dropwise and the mixture heated to 60° C. overnight. The solvent was evaporated and the residue purified by flash chromatography on silica, washing with cyclohexane and ethyl acetate. The fractions containing the desired product were concentrated under vacuum to give the title compound as a clear oil (0.198 g). LCMS m/z 361.27 [M+H]+ RT=3.80 min (Analytical Method 3).
Aufarbeitung
- customThe solvent was evaporated
- customthe residue purified by flash chromatography on silica
- washwashing with cyclohexane and ethyl acetate
- additionThe fractions containing the desired product
- concentrationwere concentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-62d9ceb81eeb411caac16488efe70c9d
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08362008B2
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