Multi-step reaction with 13 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil; tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
1.2: 3 h / 0 - 65 °C
2.1: acetic acid / 40 °C
3.1: tetrabutylammomium bromide; sodium periodate / water; dichloromethane / 3 h / 20 °C / Darkness
4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C
4.2: 1.25 h / -78 - 20 °C
5.1: copper(II) oxide; copper dichloride / water; dichloromethane / 1.5 h / -78 - -50 °C
6.1: trifluoroacetic acid / water; dichloromethane / 20 °C
7.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide; dichloromethane / 16 h / 0 - 20 °C
8.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 10 - 20 °C / Large scale
9.1: trifluoroacetic acid / 5 - 20 °C / Large scale
10.1: 1H-imidazole / dichloromethane / 3 h / -20 - 20 °C / Large scale
11.1: pyridine / dichloromethane / 3 h / -20 - 20 °C / Inert atmosphere; Large scale
12.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere; Large scale
13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 10 - 20 °C / Inert atmosphere; Large scale
With
pyridine; 1H-imidazole; dmap; sodium periodate; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; copper(II) oxide; copper dichloride;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;