Multi-step reaction with 9 steps
1.1: Isopropyl acetate; water / 20 - 30 °C / Large scale reaction
2.1: triethylamine / ethyl acetate / 0.5 h / 20 °C / Large scale reaction
3.1: lithium hydride / N,N-dimethyl-formamide / 10 - 65 °C / Large scale reaction
3.2: 5 - 30 °C / Large scale reaction
4.1: hydrogenchloride / methanol; water; toluene / 3 h / 95 °C / Large scale reaction
4.2: 1 h / 50 °C / Large scale reaction
5.1: sodium pentanolate / tetrahydrofuran / 2 h / 17 - 32 °C / Inert atmosphere; Large scale reaction
5.2: 23 h / -3 - 2 °C / Inert atmosphere; Large scale reaction
6.1: triethylamine / methanol / 0.5 h / 20 °C / Large scale reaction
7.1: Ir(COD)2BF4; Walphos SLW005-2; hydrogen / toluene / 24 h / 15 - 22 °C / 5414.51 Torr / Autoclave; Large scale reaction
8.1: N-chloro-succinimide / dichloromethane
9.1: sodium hydroxide / methanol; water / 2 h / 50 °C
With
hydrogenchloride; N-chloro-succinimide; Ir(COD)2BF4; Walphos SLW005-2; hydrogen; lithium hydride; sodium pentanolate; triethylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; Isopropyl acetate; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/op100008m