4-Toluenesulfonyl chloride → HCID 54383240, Verbindung
Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7](O)[CH3:8])=[CH:3][CH:2]=1.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(NC(C)C)(C)C.[CH3:33][C:34]([C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2)=[O:35]>C1COCC1.CCCCCC>[C:36]12([C:34](=[O:35])[CH2:33][C@@H:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH3:8])[CH2:43][CH:42]3[CH2:41][CH:40]([CH2:39][CH:38]([CH2:44]3)[CH2:37]1)[CH2:45]2Komponenten
8
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
The method followed that described in Example 9 but using (-)-(S)-1-(4-pyridyl)ethanol (1.84 g, 15.0 mmol) in THF (80 ml), butyllithium (1.6M; 9.4 ml, 15.0 mmol) in hexane, p-toluenesulfonyl chloride (2.86 g, 15.0 mmol), diisopropylamine (6.31 ml, 45.0 mmol) in THF (120 ml), butyllithium (1.6M; 28.12 ml, 45.0 mmol) in hexane and 1-adamantyl methyl ketone (8.0 g, 45 mmol). Chromatography, on elution with petrol-ether-triethylamine 100:50:1 gave the title compound (765 mg, 18%), which crystallised from hexane. m.p. 46°-48° C.; [α]D +6.8° (c 1.0, MeOH). IR, NMR and MS data were the same as given in Example 14.
Aufarbeitung
- washChromatography, on elution with petrol-ether-triethylamine 100:50:1
Quellen und Nachweise
- ORD-Eintrag
- ord-7de453a8f75a4c46966a5aafdd216cf3
- Quelldatensatz
- uspto-grants-1997_01
- Patentnummer
- US05595995
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