Lithium hexamethyldisilazane → HCID 44196480, Verbindung
Reaktionsgleichung
[CH2:1]([C:3]1[CH2:4][CH2:5][CH:6]([N+:15]([O-:17])=[O:16])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[CH2:1]([C:3]1[CH2:4][CH2:5][C@H:6]([N+:15]([O-:17])=[O:16])[C@H:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:8]=1)[CH3:2]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a flame dried round bottomed flask under nitrogen was added 250 mg (1.07 mmol) 6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine as a mixture of cis and trans isomers and 5 ml of anhydrous THF (TLC rf.=Trans 0.6; Cis 0.4; eluting solvent hexane:ethylacetate/50:50). The reaction mixture was cooled to −78° C. and 1.07 ml (1.07 mmol) of 1N lithium bis(trimethylsilyl)amide solution in THF was introduced. The reaction mixture was stirred for 20 min, and then quenched directly into a well stirred solution of 2 gm Baker Silica Gel (40 uM Flash Chromatography Packing). The solids were filtered and the filtrate was concentrated in vacuo to afford an orange red oil, 0.23 gm (92%) as the desired cis isomer, Cis-6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine (TLC rf.=0.4, hexane:ethylacetate/50:50). Mass spectrum APCI (m/z) 233 (p+1).