1: With potassium hydroxide in tetrahydrofuran; water T=20°C; 12.5 h; 2: With trifluoroacetic acid in dichloromethane 12 h;

1: With hydrogenchloride in methanol T=20°C; 24 h; 2: With potassium hydroxide in water T=20°C; 20 h; Further stages.;

trifluoroacetic acid in dichloromethane T=20°C; 15 h; Inert atmosphere;

1: With water; potassium hydroxide in tert-butyl alcohol T=120°C; 6.5 h; Inert atmosphere; 2: With hydrogenchloride; water T=20°C; Inert atmosphere;

trifluoroacetic acid in dichloromethane a.) 0 deg C, 0.5h, b.) r.t., 0.25h;

ammonia; lithium in tetrahydrofuran T=-78°C; Yield given;

1: 4.24 g / ethylenediammonium diacetate / propan-2-ol / 16 h / Ambient temperature 2: 2.27 g / H2O / dioxane / 15 h / Heating 3: 41 percent / BBr3 / CH2Cl2 / 1.) -40 deg C to 0 deg C, 1 h, 2.) 0 deg C, 30 min 4: 83 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 25 h / Ambient temperature 5: 97 percent / NaBH4 / propan-2-ol / 0.67 h / Heating 6: 85 percent / 2 h / 270 °C 7: 51 mg / K2CO3, methanol / 1 h / Ambient temperature 8: 35.8 mg / 1 N n-Bu4NF / tetrahydrofuran / 0.67 h / Ambient temperature 9: 34 mg / 8 N Jones reagent / acetone / 0.08 h / 0 °C 10: 23 mg / diethyl ether 11: 40 percent / 38 percent NaOH, MeOH / 14 h / Heating View Scheme

ammonia; lithium in tetrahydrofuran T=-78°C; Reduction; 0.5 h;

1: With jones reagent Jones oxidation; 2: With sodium hydroxide 18 h; Heating; 3: With Dowex 50WX-200

1.1: CuCN / tetrahydrofuran / 0.75 h / -78 °C 2.1: O3 / CH2Cl2; methanol / -116 °C 2.2: dimethyl sulfide / CH2Cl2; methanol / 2 h / -116 - 20 °C 3.1: diethyl ether / 0.25 h / 0 °C 4.1: 63 percent / KHMDS / tetrahydrofuran / 1.5 h / -78 °C 5.1: 96 percent / triethylsilane; LiCl / (PPh3)4Pd / dimethylformamide / 2 h / 55 °C 6.1: LiOH / tetrahydrofuran / 10 h / 0 - 20 °C 7.1: 0.0168 g / TFA / CH2Cl2 / 10 h View Scheme