Multi-step reaction with 11 steps
1.1: 1-phenylpropylamine / acetonitrile; tert-butyl methyl ether / 6 h / 20 °C
1.2: 0 °C
2.1: thionyl chloride / 1,2-dichloro-ethane / 1 h / 0 - 20 °C / Reflux
2.3: 1 h / 0 °C
3.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 0 - 70 °C
4.1: acetonitrile / 50 °C
5.1: magnesium sulfate; potassium permanganate / water; acetone / 16 h / 0 - 20 °C
6.1: potassium hexamethylsilazane / tetrahydrofuran / 1 h / -78 °C
6.2: -78 - 20 °C / Inert atmosphere
7.1: sodium carbonate / water; toluene; ethanol / 0.33 h / Inert atmosphere
7.2: 1 h / 65 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / methanol
9.1: hydrogenchloride / methanol; dichloromethane / 20 °C
9.2: CHIRAL IA; DEA
10.1: lithium hydroxide monohydrate; water / methanol; tetrahydrofuran / 2 h / 80 °C
11.1: hydrogenchloride / diethyl ether / 0.17 h
With
hydrogenchloride; potassium permanganate; thionyl chloride; lithium hydroxide monohydrate; dimethylsulfide borane complex; palladium 10% on activated carbon; 1-phenylpropylamine; water; hydrogen; potassium hexamethylsilazane; sodium carbonate; magnesium sulfate;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; tert-butyl methyl ether; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile;