Multi-step reaction with 10 steps
1.1: 89 percent / NaHCO3; 3-chloroperbenzoic acid / CH2Cl2 / 20 h / 20 °C
2.1: HCl; water / 48 h / Heating
2.2: 5.29 g / pyridinium chlorochromate / CH2Cl2 / 2 h
3.1: 91 percent / H2 / Pd/C / methanol / 15 h / 20 °C / 760 Torr
4.1: 92 percent / NaBH4 / methanol / 1 h / 0 °C
5.1: 64 percent / Pb3O4 / 1 h / 190 - 200 °C / 150.01 Torr
6.1: BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C
6.2: 27 percent / tetrahydrofuran; hexane / 2 h / 0 °C
7.1: 60 percent / H2 / Pd/C / ethyl acetate / 1 h / 20 °C / 760 Torr
8.1: 47 percent / BH3 / tetrahydrofuran / 7 h / 0 °C
9.1: 90 percent / HCl; water / 20 h / Heating
10.1: 74 percent / 1H-imidazole / dimethylformamide / 40 h / 20 °C
With
1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; lead(II,IV) oxide; borane; water; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
1.1: Baeyer-Villiger oxidation;
DOI:10.1002/hlca.200490202