Multi-step reaction with 11 steps
1.1: acetic acid / dichloromethane / 0.5 h / -5 °C / Inert atmosphere
1.2: 2 h / -5 °C / Inert atmosphere
2.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 23 °C / Inert atmosphere
3.1: hydrogenchloride / cyclopentyl methyl ether / 24 h / 0 - 20 °C / Inert atmosphere
4.1: 2-methyltetrahydrofuran; cyclopentyl methyl ether / 20 °C / Inert atmosphere
5.1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / 0 - 5 °C / Inert atmosphere
6.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
7.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
8.2: 5 - 20 °C / Inert atmosphere
9.1: water; lithium hydroxide / tetrahydrofuran / 5 - 35 °C / Inert atmosphere
10.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere
10.2: 19 h / 0 - 20.2 °C / Inert atmosphere
11.1: hydrogenchloride / dichloromethane; cyclopentyl methyl ether / Inert atmosphere
With
4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; water; sodium hexamethyldisilazane; potassium carbonate; acetic acid; lithium hydroxide;
toluene-4-sulfonic acid;
In
tetrahydrofuran; 2-methyltetrahydrofuran; dichloromethane; cyclopentyl methyl ether; water; N,N-dimethyl-formamide;