Multi-step reaction with 11 steps
1.1: hydrogenchloride; platinum(IV) oxide; hydrogen / methanol / 70 °C / 2585.81 Torr
2.1: triethylamine / dichloromethane / 0 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / 0.17 h / -78 °C
3.2: 0.25 h / -78 °C
4.1: lithium borohydride; methanol / tetrahydrofuran / -10 - 20 °C
5.1: carbon dioxide / methanol
6.1: palladium 10% on activated carbon; hydrogen / ethanol
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 50 °C
8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 - 20 °C / Inert atmosphere
9.1: sodium hydroxide; methanol / tetrahydrofuran / 20 °C
10.1: sodium hydride / dimethyl sulfoxide / 45 °C
11.1: methanol / 50 - 60 °C
With
hydrogenchloride; methanol; platinum(IV) oxide; lithium borohydride; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; carbon dioxide; palladium 10% on activated carbon; hydrogen; sodium hydride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
3.1: |Swern Oxidation;