1: 95 percent / p-TsOH / 1 h / Ambient temperature 2: 92 percent / LiAlH4 / diethyl ether / 16 h / Ambient temperature 3: 1) potassium hydride / 1) THF, 0 deg C, 30 min, 2) THF, RT, 16 h 5: tri-n-butylphosphine / CH2Cl2 / 0 deg C, 4 h then RT, 6 h 6: 4 M aq. HCl / CH2Cl2 / 1 h / 0 °C 7: 100 percent / N-(p-toluenesulfonyl)phenyloxaziridine, diisopropylamine / CHCl3 / 1) 0 deg C, 1.5 h, 2) RT, 20 h, 3) reflux, 1 h 8: 67 percent / pyridinium dichromate / dimethylformamide / 36 h / Ambient temperature 9: 1) ozone, 2) NaBH4 / 1) MeOH, CH2Cl2, -78 deg C, 5 min, 2) 20 h, 0 deg C 10: 88 percent / ammonium formate / 10 percent Pd/C / methanol / 2 h / Heating View Scheme

1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine in 1,2-dichloro-ethane; benzene T=75 - 80°C; 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: NaH / tetrahydrofuran / -78 - 0 °C 2: K2CO3 / methanol / Ambient temperature 3: Bu3SnH, Et3B / toluene / 0.08 h / 0 °C View Scheme

1: organotin phosphate condensates (OPC) / hexane / Heating 2: 1.) CH2Cl2, N,N-dimethylformamide dimethylacetale, reflux, 12 h, 2.) acetic anhydride, reflux, 1 h 3: 88 percent / Na, NH3 / diethyl ether / 0.5 h / -78 °C View Scheme

1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine in 1,2-dichloro-ethane; benzene T=75 - 80°C; 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

lithium aluminium tetrahydride in tetrahydrofuran T=-40 - 20°C;

zeolite (H-ZSM 5); sodium cyanoborohydride in 1,2-dichloro-ethane 8 h; Heating; Yield givenYields of byproduct given;