sodium hydrogencarbonate in methanol; acetone 24 h; Ambient temperature;

in dichloromethane; water T=0°C; 1 h; Yield given;

1: 87 percent / TsOH / benzene / 5 h / Heating 2: 36 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 19 h / 70 °C 3: 92 percent / K2CO3 / methanol / 5 h / Ambient temperature 4: 93 percent / PPh3, CCl4 / CH2Cl2 / 19 h / Ambient temperature 5: 25percent HCO2NH4 / tetrahydrofuran / 20.5 h / 0 °C 6: 3M HCl / ethyl acetate 7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 8: 97 percent / DBU / acetonitrile / Ambient temperature 9: 90 percent / 1M HBr / acetonitrile / 1.5 h / Ambient temperature 10: 1.) Et3N / 1.) 0 deg C, 1 h; 2.) 0 deg C - r.t. View Scheme

1: 57 percent / NaBH4 / various solvent(s) / 2.5 h / 0 °C 2: 81 percent / camphorsulfonic acid / toluene / 1 h / 50 °C View Scheme

1: Et3N / CH2Cl2 / 0.5 h / -78 °C 2: CH2Cl2 / 1 h / 0 °C View Scheme

1: 81 percent / n-Bu4NF / tetrahydrofuran / 1 h / 20 °C 2: hydrobromic acid / acetonitrile / 2 h / 20 °C 3: Et3N / CH2Cl2 / 0.5 h / -78 °C 4: CH2Cl2 / 1 h / 0 °C View Scheme

triethylamine 1.) 0 deg C, 1 h; 2.) 0 deg C - r.t.; Yield given. Multistep reaction;