Multi-step reaction with 9 steps
1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 20 °C
2.1: triethylamine / 1,2-dichloro-ethane / 20 °C
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 35 °C / sodium phosphate buffer
3.2: 20 °C
4.1: diazomethyl-trimethyl-silane / dichloromethane; diethyl ether / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 0.5 h / -78 °C / Inert atmosphere
5.3: 0.5 h / -78 °C
6.1: thionyl chloride; pyridine / toluene / 0.75 h / 20 - 90 °C
7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; tetrahydrofuran / 20 °C
7.2: 0.5 h / 20 °C / Inert atmosphere
8.1: methanol / titanium(IV)isopropoxide; acetic acid / 1,2-dichloro-ethane / 1 h / 20 °C / Inert atmosphere
8.2: 5.5 h / 20 °C
9.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
9.2: pH 8
9.3: pH 5
With
pyridine; methanol; N-chloro-succinimide; osmium(VIII) oxide; chloro-trimethyl-silane; thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diazomethyl-trimethyl-silane;
titanium(IV)isopropoxide; acetic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;