Multi-step reaction with 13 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 0.5 h / 20 °C / Inert atmosphere
2.1: trifluoroacetic acid / tetrahydrofuran; dichloromethane / 16 h / 20 °C / Inert atmosphere
3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
4.1: 16 h / Reflux; Inert atmosphere
5.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0.67 h / 0 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere
7.1: sodium hydrogencarbonate / water; acetone / 4 h / 20 °C / Inert atmosphere
8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C / Inert atmosphere
9.1: piperidine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
10.1: trifluoroacetic acid / dichloromethane; water / 3 h / 0 °C / Inert atmosphere
11.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere
12.1: Acetyl bromide / dichloromethane / 4 h / 20 °C / Inert atmosphere
13.1: potassium carbonate / ethylene glycol; 1,2-dimethoxyethane / 0.05 h / 20 °C / Inert atmosphere
With
piperidine; dmap; lithium hydroxide monohydrate; Acetyl bromide; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydrogencarbonate; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethylene glycol; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm301346z