1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 8 h / 20 °C / |Inert atmosphere 2.1: trifluoroacetic acid; dimethylsulfide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 2.2: 0.5 h / 50 °C / |Inert atmosphere 3.1: acetic acid; sodium cyanoborohydride / methanol / 1 h / 20 °C / |Inert atmosphere View Scheme

Multi-step reaction with 14 steps 1.1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere1.2: 2 h / -78 - 0 °C / |Inert atmosphere2.1: hydrazine hydrate / tetrahydrofuran / 1 h / 0 °C3.1: hydrogenchloride; tert.-butylnitrite / ethyl acetate; isopropyl alcohol / 1 h / 60 °C / |Inert atmosphere4.1: titanium tetrachloride; triethylsilane / dichloromethane / 1 h / 0 °C / |Inert atmosphere5.1: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / |Inert atmosphere6.1: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C7.1: Grubb's 2nd generation catalyst / toluene / 1 h / 80 °C / |Inert atmosphere8.1: tetrakis(triphenylphosphine) palladium(0); silver carbonate / toluene / 4 h / 100 °C / |Inert atmosphere9.1: methanol; magnesium / benzene / 1 h / 20 °C / |Inert atmosphere10.1: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 1 h / 20 °C / |Inert atmosphere11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere12.1: [bis(acetoxy)iodo]benzene / acetic acid / 1 h / 20 °C / |Inert atmosphere13.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / tert-butyl alcohol; tetrahydrofuran; water / 4 h / 20 °C14.1: diethyl ether; methanol / 0.25 h / 20 °C / |Inert atmosphere  

With  1,8-diazabicyclo[5.4.0]undec-7-ene in  methanol