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29th August 2013 @ 14:54

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Reaction information

*#Reaction file
reactionscheme_23b.cdx
*Reaction file type CDX
*Procedure

 

Dry Cs2CO3 (0.85 g, 2.6 mmol), dppf (0.11 g, 0.20 mmol), PhBr (0.33 g, 2.0 mmol) and pyrrolidine (0.71 g, 10 mmol) were added to a 30 mL Schlenk tube under argon. Dry, de-gassed toluene (10 mL) was added, followed by tBuNC (0.34 mL, 3.0 mmol) and finally PdCl2 (17.7 mg, 0.10 mmol) was added against a flow of argon. Another aliquote of toluene (10 mL) was added and the tube fitted with a stopper. The mixture was heated with stirring at 109 °C for 4 h. After cooling to room temperature, the reaction mixture was added to ether (20 mL) and the resulting slurry filtered to give a dark-brown solution which was extracted with dilute acetic acid (2.5% in water, 6x5 mL). The combined aqueous extractions were washed with ether (2x10 mL), then treated with a concentrated KOH-solution (30 mL) in presence of ether (20 mL). The ethereal layer was collected and the aqueous layer extracted with ether (3x30 mL). The combined ether phases were dried over MgSO4 before evaporation. Kugelrohr distillation (oven temp 100–110 °C / 1 mmHg) gave the title compound as a pale yellow oil which crystallised to a white solid (0.36 g, 78%).
*Yield (%) 78 %
*Type of Yield Isolated pure product
Reference(s)
Gustaf Saluste p89-90.pdf
Further information  

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For step in multistep reaction - link to following reaction step Reaction 31B: Synthesis by tert-butyl deprotection of phenyl(tetrahydro-1H-1-pyrrolyl)methanimine 
Attached Files
reactionscheme_23b.cdx