hydrogen; triethylamine; palladium 10 on activated carbon in ethanol 7 h;

lithium aluminium tetrahydride in diethyl ether T=-78°C; 0.5 h;

methanol; sodium tetrahydroborate T=20°C; 3 h;

1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight 2: thionyl chloride / Heating 3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 5: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 6: 66 percent / potassium permanganate / H2O / 3 h / Heating 7: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 8: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: 66 percent / potassium permanganate / H2O / 3 h / Heating 2: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 3: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 2: 66 percent / potassium permanganate / H2O / 3 h / Heating 3: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 4: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: thionyl chloride / Heating 2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 4: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 5: 66 percent / potassium permanganate / H2O / 3 h / Heating 6: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 7: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 2: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 3: 66 percent / potassium permanganate / H2O / 3 h / Heating 4: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 5: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme

1: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 2: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 3: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min 4: 66 percent / potassium permanganate / H2O / 3 h / Heating 5: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight 6: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C View Scheme