in tetrahydrofuran T=20°C; 24 h;

1: N-acetyl-5-methoxytryptamine With n-butyllithium in tetrahydrofuran; hexane T=-19°C; deprotonation; 4 h; 2: N,N-dimethyl acetamide in tetrahydrofuran; hexane T=-19°C; Acetylation; 1 h;

1.1: 97 percent / Et3SiH / trifluoroacetic acid / 3 h / 60 °C 2.1: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C 3.1: 94 percent / BF3 / 0.67 h / Heating 4.1: 99 percent / aq. NaOH / methanol / 4 h / Heating 5.1: 92 percent / pyridine / 0.67 h / 20 °C 6.1: n-BuLi / hexane; tetrahydrofuran / 4 h / -19 °C 6.2: 30 percent / hexane; tetrahydrofuran / 1 h / -19 °C View Scheme

1.1: 65 percent / H2O2 / Na2WO4*2H2O / methanol; H2O / 0.5 h / 20 °C 2.1: 94 percent / BF3 / 0.67 h / Heating 3.1: 99 percent / aq. NaOH / methanol / 4 h / Heating 4.1: 92 percent / pyridine / 0.67 h / 20 °C 5.1: n-BuLi / hexane; tetrahydrofuran / 4 h / -19 °C 5.2: 30 percent / hexane; tetrahydrofuran / 1 h / -19 °C View Scheme

1.1: 92 percent / pyridine / 0.67 h / 20 °C 2.1: n-BuLi / hexane; tetrahydrofuran / 4 h / -19 °C 2.2: 30 percent / hexane; tetrahydrofuran / 1 h / -19 °C View Scheme

1.1: 94 percent / BF3 / 0.67 h / Heating 2.1: 99 percent / aq. NaOH / methanol / 4 h / Heating 3.1: 92 percent / pyridine / 0.67 h / 20 °C 4.1: n-BuLi / hexane; tetrahydrofuran / 4 h / -19 °C 4.2: 30 percent / hexane; tetrahydrofuran / 1 h / -19 °C View Scheme

1.1: 99 percent / aq. NaOH / methanol / 4 h / Heating 2.1: 92 percent / pyridine / 0.67 h / 20 °C 3.1: n-BuLi / hexane; tetrahydrofuran / 4 h / -19 °C 3.2: 30 percent / hexane; tetrahydrofuran / 1 h / -19 °C View Scheme

in tetrahydrofuran T=20°C; 2 h;