1: 100 percent / H2 / Pd/C / ethanol 2: 64 percent / PBr3 / diethyl ether / 0 °C View Scheme

Pd-C in ethyl acetate

1.1: [3H]-Caproic acid / ethanol / 70 - 150 °C / |Reflux 2.1: iodine / acetonitrile / 24 h / 0 °C / |Inert atmosphere; |Darkness 3.1: sodium carbonate / methanol / |Inert atmosphere; |Reflux 4.1: (S,S)-(salen)Co(OAc) complex; water / 12 h / 0 - 25 °C / |Resolution of racemate 5.1: triethylamine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 °C 7.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 8.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 9.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 10.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 10.2: 0.25 h / 20 °C / |Inert atmosphere 11.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 11.2: 48 h / 0 °C / |Inert atmosphere 12.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 13.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

hydrogen; palladium on activated charcoal in ethanol