T=110°C; 0.5 h; Ionic liquidMicrowave irradiation; TemperatureTimeSolventConcentration;

triethylamine in dichloromethane T=0 - 20°C; Inert atmosphere;

toluene-4-sulfonic acid; tetrakis(triphenylphosphine) palladium(0) T=100°C; P=15001.2 Torr; 4 h;

isobutyramide; tetra(n-butyl)ammonium hydroxide T=100°C; 1 h; 1) pH 10 - 12;

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 5.2: 20 °C View Scheme

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -40 °C / |Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / |Reflux; |Dean-Stark 3.1: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: HLAP; water / aq. buffer / 48 h / 40 °C / pH 7.5 / |Enzymatic reaction View Scheme

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 5.2: 20 °C 6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux 8.1: N,N-dimethyl acetamide / 24 h / 25 °C / Inert atmosphere 9.1: triethylamine / 4-(N,N-dimethlyamino)pyridine / 3 h / Inert atmosphere 10.1: trifluoroacetic acid / 1 h / 20 °C / Inert atmosphere 11.1: triethylamine; hydrogen / [Rh(S)-phanephos(cod)]BF4 / ethanol / 6 h / 60 °C / 22502.3 Torr / Autoclave 12.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 80 °C / Inert atmosphere 12.2: 8 h / 50 °C / Reflux 13.1: hydrogenchloride; water / ethanol / 48 h / 70 °C 14.1: hydrogen / palladium 10 on activated carbon / methanol / 12 h / 760.05 Torr 14.2: Inert atmosphere View Scheme

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 5.2: 20 °C 6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux View Scheme