1: With mercury(II) perchlorate in tetrahydrofuran T=20°C; Schmidt reaction; 0.75 h; 2: With sodium hydroxide; sodium tetrahydroborate in tetrahydrofuran; water 2 h; Further stages.;

di-tert-butyl peroxide T=125°C;

acetic acid; platinum Hydrogenation;

1: sodium amide; pentyl bromide 2: platinum; acetic acid / Hydrogenation View Scheme

1.1: propionic acid / toluene / 18 h / 100 °C 2.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.1: Et3N / CH2Cl2 / 0.33 h / -50 - -20 °C 4.1: 0.66 g / NaN3 / dimethylsulfoxide / 16 h 5.1: mercuric perchlorate trihydrate / tetrahydrofuran / 0.75 h / 20 °C 5.2: 58 percent / sodium borohydride; sodium hydroxide / H2O; tetrahydrofuran / 2 h View Scheme

1.1: Et3N / CH2Cl2 / 0.33 h / -50 - -20 °C 2.1: 0.66 g / NaN3 / dimethylsulfoxide / 16 h 3.1: mercuric perchlorate trihydrate / tetrahydrofuran / 0.75 h / 20 °C 3.2: 58 percent / sodium borohydride; sodium hydroxide / H2O; tetrahydrofuran / 2 h View Scheme

1.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.1: Et3N / CH2Cl2 / 0.33 h / -50 - -20 °C 3.1: 0.66 g / NaN3 / dimethylsulfoxide / 16 h 4.1: mercuric perchlorate trihydrate / tetrahydrofuran / 0.75 h / 20 °C 4.2: 58 percent / sodium borohydride; sodium hydroxide / H2O; tetrahydrofuran / 2 h View Scheme

ethanol; nickel Hydrogenation;

1: benzene / Hydrieren des Reaktionsprodukts an Palladium/Strontiumcarbonat in Butanon und Erwaermen der Reaktionsloesung 2: Raney nickel; ethanol / Hydrogenation View Scheme

T=122 - 125°C;