sodium tetrahydroborate in tetrahydrofuran; methanol T=20°C; 18 h;

n-butyllithium in tetrahydrofuran multistep reaction; various reaction conditions (temp., and amine base); Product distribution;

1: o-tolualdehyde tert-butylimine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=0°C; 1.16667 h; Inert atmosphere; 2: benzonitrile in tetrahydrofuran; hexane T=-78°C; 0.05 h; Inert atmosphere; 3: methyl iodide Further stages;

1.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 1.17 h / 0 °C 1.2: 0.05 h / -78 °C 2.1: tetrahydrofuran; hexane / 0.5 h 2.2: 23 °C View Scheme

1: o-tolualdehyde tert-butylimine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=0°C; 1.16667 h; Inert atmosphere; 2: benzonitrile in tetrahydrofuran; hexane T=-78°C; 0.05 h; Inert atmosphere; Further stages;

1: o-tolualdehyde tert-butylimine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran; hexane T=0°C; 0.666667 h; Inert atmosphere; 2: benzonitrile in tetrahydrofuran; hexane T=-78 - 23°C; Inert atmosphere;

1.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 1.17 h / 0 °C 1.2: 0.05 h / -78 °C 2.1: trifluoroacetic acid / tetrahydrofuran; hexane / 23 °C View Scheme