4-(N,N-dimethlyamino)pyridine in acetonitrile T=20°C; Decarboxylation; 3 h;

β-cyclodextrin in methanol; acetone T=20°C; 0.166667 h;

1: tert-butyl acetyl(benzyl)carbamate With diisobutylaluminium hydride in tetrahydrofuran; hexane T=-78°C; 2: With methanol in tetrahydrofuran; hexane 0.5 h; 3: acrylic acid methyl ester With samarium diiodide; boron trifluoride diethyl etherate in tetrahydrofuran; hexane; tert-butyl alcohol T=-40°C; Michael addition;

1: N-(tert-butyloxycarbonyl)-N-methylbenzylamine With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran T=-78°C; 2 h; 2: methyl iodide in tetrahydrofuran

1: tert-butyl ethyl(methyl)carbamate With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in diethyl ether; cyclohexane T=-60°C; 1 h; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran; diethyl ether; cyclohexane T=-60 - 20°C; 1.5 h; Inert atmosphere; 3: bromobenzene With tris-(dibenzylideneacetone)dipalladium(0); PtBu3*HBF4 in toluene 17 h; Inert atmosphere;

4-(N,N-dimethlyamino)pyridine in acetonitrile T=20°C; Condensation; 0.5 h;

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 1 h / -60 °C 1.2: 0.5 h / -60 °C 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 1 h / -60 °C / |Inert atmosphere 2.2: 1.5 h / -60 - 20 °C / |Inert atmosphere 2.3: 17 h / |Inert atmosphere View Scheme

1.1: triethylamine / water; tetrahydrofuran / 6.17 h / 0 - 20 °C 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 1 h / -60 °C 2.2: 0.5 h / -60 °C 3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether; cyclohexane / 1 h / -60 °C / |Inert atmosphere 3.2: 1.5 h / -60 - 20 °C / |Inert atmosphere 3.3: 17 h / |Inert atmosphere View Scheme

4-(N,N-dimethlyamino)pyridine in acetonitrile T=20°C; Condensation; 0.0833333 h; Product distribution; Further Variations:TemperaturesSolventsReagentsreaction times;