Multi-step reaction with 10 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / 0.17 h / -78 °C
1.2: 0.25 h / -78 °C
2.1: lithium borohydride; methanol / tetrahydrofuran / -10 - 20 °C
3.1: carbon dioxide / methanol
4.1: diethylazodicarboxylate; 4-(N,N-Dimethylamino)triphenylphosphine / tetrahydrofuran / -25 - 20 °C / Inert atmosphere
5.1: sodium hydroxide; water / tetrahydrofuran; methanol
6.1: palladium 10% on activated carbon; hydrogen / ethyl acetate
7.1: sodium hydride / dimethyl sulfoxide / 0.25 h
7.2: 40 °C
8.1: tetrakis(triphenylphosphine) palladium(0); bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 130 °C / Inert atmosphere; Sealed tube
9.1: hydrogenchloride / 1,4-dioxane; dichloromethane / -78 - 20 °C
10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 50 °C
With
hydrogenchloride; methanol; lithium borohydride; tetrakis(triphenylphosphine) palladium(0); 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; bis(tri-t-butylphosphine)palladium(0); carbon dioxide; palladium 10% on activated carbon; water; hydrogen; sodium hydride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; diethylazodicarboxylate; 4-(N,N-Dimethylamino)triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;
1.1: |Swern Oxidation;