1: With n-butyllithium; diisopropylamine; sodium bromide in tetrahydrofuran; hexanes T=-78 - 0°C; 1.16667 h; 2: With iodine in tetrahydrofuran; hexanes T=-78°C; 2 h;

piperidine; n-butyllithium in tetrahydrofuran; hexane T=-75°C; 20 h;

1.1: lithium N,N-diisopropylcarbamate; diisopropylamine; lithium bromide / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 67 percent / iodine / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: 46 percent / piperidine; butyllithium / tetrahydrofuran; hexane / 20 h / -75 °C View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-75°C; 0.25 h;

1: 65 percent / butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 2: 87 percent / ammonium formate / palladium (10 percent on charcoal) / methanol / 0.25 h / 25 °C View Scheme