Multi-step reaction with 14 steps
1.1: sodium hydrogencarbonate / water / 0.5 h / 20 °C
1.2: 4.5 h / 20 °C
2.1: pyridine / 0 - 20 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C
4.1: zinc; acetic acid / dichloromethane; methanol / 1 h / 0 - 20 °C / Inert atmosphere
5.1: sodium methylate / dichloromethane; methanol / 2 h / 20 °C
5.2: pH ~ 7
6.1: potassium carbonate; triflic azide / zinc(II) chloride / dichloromethane; water; methanol / 20 °C
7.1: camphorsulfonic acid / toluene / 2 h / 20 °C
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 20 °C
9.1: trifluorormethanesulfonic acid; triethylsilane / dichloromethane / 1 h / -78 °C
10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C
10.2: 2 h / 20 °C
11.1: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 20 °C
12.1: sodium hydrogencarbonate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
13.1: water; ammonium cerium (IV) nitrate / acetonitrile / 2 h / 0 - 20 °C / Inert atmosphere
14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 0 - 20 °C
With
pyridine; triethylsilane; ammonium cerium (IV) nitrate; trifluorormethanesulfonic acid; triflic azide; boron trifluoride diethyl etherate; water; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; zinc; trimethylphosphane;
zinc(II) chloride;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;