Multi-step reaction with 17 steps
1.1: triethylamine / dichloromethane / 20 °C
2.1: lithium borohydride / tetrahydrofuran / 2 h / 0 - 50 °C
2.2: 0 - 20 °C
3.1: 1H-imidazole / dichloromethane / 0 - 20 °C
4.1: sodium bromate; ruthenium(IV) oxide hydrate / ethyl acetate; water / 20 - 55 °C
5.1: water; sodium tetrahydroborate / isopropyl alcohol / 20 °C
6.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
7.1: acetic acid / methanol / 0.5 h / 20 °C
7.2: 20 °C
8.1: sodium hydrogencarbonate / chloroform; water / 1 h / 20 °C
9.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Molecular sieve
9.2: 3 h / 20 °C
10.1: N-fluorobis(benzenesulfon)imide; 5-benzyl-2,2,3-trimethylimidazolidin-4-one dichloroacetic acid salt / isopropyl alcohol; tetrahydrofuran / 24 h / -20 °C
11.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
12.1: trifluoroacetic acid / 1,2-dichloro-ethane / 1 h / 0 °C
13.1: sodium hydrogencarbonate / water; tetrahydrofuran / 0 - 20 °C
14.1: hydrogen / palladium 10% on activated carbon / methanol / 3 h / 760.05 Torr
15.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
17.1: hydrogen / 20% palladium hydroxide-activated charcoal / ethyl acetate; ethanol / 3 h / 760.05 Torr
With
1H-imidazole; hydrogenchloride; sodium bromate; sodium tetrahydroborate; lithium borohydride; ruthenium(IV) oxide hydrate; 5-benzyl-2,2,3-trimethylimidazolidin-4-one dichloroacetic acid salt; tetrabutyl ammonium fluoride; water; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; N-fluorobis(benzenesulfon)imide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; isopropyl alcohol;