Tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate → 1207840-16-1
Reaktionsgleichung
Br[C:2](Br)=[CH:3][CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1.C([Li])CCC>>[CH2:4]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)[C:3]#[CH:2]Komponenten
3
Reaktionsbedingungen
- Temperatur
- -80 °C
Versuchsvorschrift
A flask was charged with tert-butyl 3-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate (155 g, 420. mmol) and (1,800 ml) and cooled to −80° C. A solution of butyllithium (370 ml, 2.20 equiv) was added dropwise such that the internal temperature was maintained at −80° C. After stirring for an addition hour at −80° C., the reaction mixture was quenched by the addition of 1,000 mL of saturated aqueous ammonium chloride. The resulting mixture was extracted with diethyl ether (3×1,000 mL). The combined organic layers were washed with brine (3×800 mL), then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether gradient) to afford tert-butyl 3-(prop-2-ynyl)pyrrolidine-1-carboxylate as light yellow oil.