Rivaroxaban-d4 synthesis

Yield:-

Steps:

Multi-step reaction with 8 steps
1.1: copper(l) iodide / 8 h / 90 - 110 °C
2.1: sodium hydroxide / ethanol; water / 1.5 h / 0 - 50 °C / pH 10 - 13
3.1: sulfuric acid / 0.5 h / 20 - 30 °C
3.2: 1 h / -5 - 10 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 40 - 50 °C
5.1: ethanol; water / 32 h / 0 °C / Reflux
6.1: dichloromethane / 10 h / 20 - 30 °C
6.2: 1 h / 20 - 30 °C
7.1: methylamine / ethanol / 6 h / 20 - 70 °C
8.1: sodium carbonate / dichloromethane / 6 h / 20 - 30 °C

References:

CN107857761,2018,A