Multi-step reaction with 9 steps
1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water; dimethoxyethane-1,2 / 20 - 85 °C / Inert atmosphere
2.1: hydrogen / palladium on activated charcoal / ethanol; water / 60 °C / 37503.8 Torr / Inert atmosphere
3.1: dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: water; lithium hydroxide / tetrahydrofuran / 20 - 60 °C
4.2: pH 1
5.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 0 - 20 °C
5.2: Cooling with ice
6.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C
6.2: 1 h / 0 - 20 °C
7.1: sodium azide / N,N-dimethyl-formamide / 70 °C / Inert atmosphere
8.1: hydrogen / palladium on activated charcoal / ethanol; water / 24 h / 20 °C / 760.05 Torr
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
With
sodium tetrahydroborate; sodium azide; boron trifluoride diethyl etherate; water; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
tetrakis(triphenylphosphine) palladium(0); palladium on activated charcoal;
In
tetrahydrofuran; dimethoxyethane-1,2; ethanol; dichloromethane; water; N,N-dimethyl-formamide;