Multi-step reaction with 17 steps
1.1: iodine / 12 h / 20 °C
2.1: ammonia / tetrahydrofuran / 14 h / 0 - 20 °C
3.1: potassium carbonate / dichloromethane / 0.67 h / 20 °C
4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.67 h / 20 °C / Inert atmosphere
5.1: sodium azide / N,N-dimethyl-formamide / 4 h / 65 °C / Inert atmosphere
6.1: acetyl chloride; methanol / 12 h / 0 - 20 °C
7.1: 12 h / 20 °C
8.1: sodium hydride / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; mineral oil / 0.08 h / 0 °C
8.2: 12.5 h / 0 - 20 °C
9.1: trifluoroacetic acid; water / tetrahydrofuran / 12 h / 20 °C
10.1: 10-camphorsufonic acid / acetonitrile / 0.33 h / 20 °C
11.1: water / acetonitrile / 0.33 h / 20 °C
12.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.17 h / 20 °C / Inert atmosphere
13.1: sodium methylate; methanol / tetrahydrofuran / 2 h / 40 °C
14.1: Amberlyst.(R). 15 hydrogen form resin / 0.5 h / 20 °C
15.1: pyridine / 1.17 h / 20 °C
16.1: water; acetic acid / 12 h / 20 °C
17.1: 10-camphorsufonic acid / acetonitrile / 0.33 h / 20 °C
With
pyridine; methanol; sodium azide; trimethylsilyl trifluoromethanesulfonate; 10-camphorsufonic acid; ammonia; water; iodine; sodium methylate; sodium hydride; potassium carbonate; acetic acid; acetyl chloride; trifluoroacetic acid;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;