tert-Butyl [(1S,3R,5S)-3-(3-aminopyridin-4-yl)-5-methylcyclohexyl]carbamate synthesis

Yield:-

Steps:

Multi-step reaction with 9 steps
1.1: ethanol; cerium(III) chloride heptahydrate; sodium tetrahydroborate / 1 h / 0 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
3.1: acetic acid; iron / 2 h / 20 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h
5.1: dmap / dichloromethane
6.1: hydrogenchloride / water; methanol / 6 h / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
8.1: methanol / 2 h / 20 °C
8.2: -78 - 20 °C
9.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol / 14 h
9.2: Inert atmosphere

References:

INCYTE CORPORATION;VECHORKIN, Oleg;LI, Yun-Long;ZHU, Wenyu WO2016/10897, 2016, A1