hydrogen; palladium 10 on activated carbon in ethyl acetate T=20°C;

1: With tert-butylamine in ethyl acetate T=20°C; 2: With formic acid in water; ethyl acetate pH=5;

hydrogen; 5 Pd(II)/C(eggshell) in ethyl acetate

sulfuric acid in water; acetonitrile T=15°C;

Lipase PS SD in acetone T=50 - 60°C; pH=8; 22 h; Enzymatic reaction;

1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere 1.2: -78 - -60 °C / Inert atmosphere 1.3: -78 - 10 °C 2.1: sodium tetrahydroborate; methanol / -5 - 0 °C 2.2: -5 - 0 °C / pH 5 - 6 3.1: 2,2'-azo-bisisobutyronitrile / toluene / 80 - 85 °C 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -10 - 0 °C 4.2: -10 - 0 °C 5.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / -70 - -60 °C / Inert atmosphere 5.2: 0.5 h / -50 - -40 °C / Inert atmosphere 5.3: -60 - -50 °C / Inert atmosphere 6.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C 7.2: -70 - 0 °C 8.1: trifluoroacetic acid / acetonitrile / 16 h / 15 - 30 °C 9.1: Lipase PS SD / acetone / 22 h / 50 - 60 °C / pH 8 / Enzymatic reaction View Scheme

1.1: sodium tetrahydroborate; methanol / -5 - 0 °C 1.2: -5 - 0 °C / pH 5 - 6 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 - 70 °C 3.1: 2,2'-azo-bisisobutyronitrile / toluene / 80 - 85 °C 4.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / 0.5 h / -70 - -60 °C / Inert atmosphere 4.2: 0.5 h / -50 - -40 °C / Inert atmosphere 4.3: -60 - -50 °C 5.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C 6.2: -70 - 0 °C 7.1: trifluoroacetic acid / acetonitrile / 16 h / 15 - 30 °C 8.1: Lipase PS SD / acetone / 22 h / 50 - 60 °C / pH 8 / Enzymatic reaction View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 - 70 °C 2.1: 2,2'-azo-bisisobutyronitrile / toluene / 80 - 85 °C 3.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / 0.5 h / -70 - -60 °C / Inert atmosphere 3.2: 0.5 h / -50 - -40 °C / Inert atmosphere 3.3: -60 - -50 °C 4.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C 5.2: -70 - 0 °C 6.1: sodium hydroxide; sodium dihydrogenphosphate / Lipase PS SD / acetone / 50 °C / pH 7 / Enzymatic reaction 7.1: sulfuric acid / acetonitrile; water / 15 °C View Scheme

1.1: pyridine / dichloromethane / 0 - 15 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl methyl ether / Reflux 3.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere 3.2: -78 - -60 °C / Inert atmosphere 3.3: -78 - 10 °C 4.1: sodium tetrahydroborate; methanol / -5 - 0 °C 4.2: -5 - 0 °C / pH 5 - 6 5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 - 70 °C 6.1: 2,2'-azo-bisisobutyronitrile / toluene / 80 - 85 °C 7.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / 0.5 h / -70 - -60 °C / Inert atmosphere 7.2: 0.5 h / -50 - -40 °C / Inert atmosphere 7.3: -60 - -50 °C 8.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr 9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C 9.2: -70 - 0 °C 10.1: trifluoroacetic acid / acetonitrile / 16 h / 15 - 30 °C 11.1: Lipase PS SD / acetone / 22 h / 50 - 60 °C / pH 8 / Enzymatic reaction View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl methyl ether / Reflux 2.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere 2.2: -78 - -60 °C / Inert atmosphere 2.3: -78 - 10 °C 3.1: sodium tetrahydroborate; methanol / -5 - 0 °C 3.2: -5 - 0 °C / pH 5 - 6 4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 60 - 70 °C 5.1: 2,2'-azo-bisisobutyronitrile / toluene / 80 - 85 °C 6.1: methyllithium / formaldehyde diethyl acetal; tetrahydrofuran / 0.5 h / -70 - -60 °C / Inert atmosphere 6.2: 0.5 h / -50 - -40 °C / Inert atmosphere 6.3: -60 - -50 °C 7.1: hydrogen / palladium 10 on activated carbon / ethyl acetate; water / 60 °C / 3000.3 Torr 8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -70 - -60 °C 8.2: -70 - 0 °C 9.1: trifluoroacetic acid / acetonitrile / 16 h / 15 - 30 °C 10.1: Lipase PS SD / acetone / 22 h / 50 - 60 °C / pH 8 / Enzymatic reaction View Scheme