Multi-step reaction with 11 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 6 h / Reflux
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C
2.2: 2 h / -78 - 20 °C
3.1: toluene-4-sulfonic acid / benzene / 1 h / Reflux
4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 10 h
5.1: sodium carbonate / acetone; water / 12.5 h / 0 - 20 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
6.2: 12.5 h / -78 - 20 °C
7.1: triethylamine / dichloromethane / 1.25 h / 0 °C
8.1: sodium azide / N,N-dimethyl-formamide / 2 h / 75 °C
9.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h
10.1: toluene-4-sulfonic acid / acetone; water / 6 h / Reflux
11.1: hydrogenchloride / dichloromethane; diethyl ether
With
hydrogenchloride; n-butyllithium; sodium azide; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; sodium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
2.1: |Swern Oxidation;