Multi-step reaction with 10 steps
1.1: borane-THF / tetrahydrofuran / 0 °C / Reflux
2.1: dipyridinium dichromate / dichloromethane / 16 h / 20 °C
3.1: hydrogen; sodium acetate; 20% PtO2/C / ethyl acetate / 0.5 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / ethyl acetate / -78 - 20 °C
5.1: ammonia / ethanol / 5 h / 135 °C / 1551.49 Torr
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 16 h / 80 °C
7.1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 16 h / 20 °C
8.1: boron tribromide / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
8.2: 3 h / 0 - 80 °C
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
10.1: sodium hydroxide / ethanol / 16 h / 80 °C
10.2: 20 °C / pH 3 - 4
With
dipyridinium dichromate; borane-THF; di-isopropyl azodicarboxylate; 20% PtO2/C; ammonia; hydrogen; sodium acetate; boron tribromide; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;