potassium carbonate in N,N-dimethyl-formamide T=50°C;

potassium carbonate; cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide in toluene T=100°C; 20 h;

1.1: dichloromethane; chlorobenzene / 20 °C 1.2: 0 °C 2.1: hydrogen; 4-methyl-morpholine / platinum on carbon / 4 h / Inert atmosphere 3.1: sodium hydrogencarbonate / dichloromethane; water / 1.5 h / 0 °C 4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 4.2: 20 °C 5.1: isobutyl chloroformate / acetonitrile / 20 °C 6.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C View Scheme

1.1: hydrogen; 4-methyl-morpholine / platinum on carbon / 4 h / Inert atmosphere 2.1: sodium hydrogencarbonate / dichloromethane; water / 1.5 h / 0 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 3.2: 20 °C 4.1: isobutyl chloroformate / acetonitrile / 20 °C 5.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C View Scheme

1.1: sodium hydrogencarbonate / dichloromethane; water / 1.5 h / 0 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 2.2: 20 °C 3.1: isobutyl chloroformate / acetonitrile / 20 °C 4.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 1.2: 20 °C 2.1: isobutyl chloroformate / acetonitrile / 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C View Scheme