1: methanol / HCl / Ambient temperature; also with 2-methyl and 2-phenyl derivatives 2: 87 percent / diethyl ether / 0.03 h 3: methanol / HCl View Scheme

boron trifluoride diethyl etherate; sodium cyanoborohydride in methanol 8 h; Heating;

methanol; hydrogenchloride

methanol; hydrogenchloride

1: methanol / HCl / Ambient temperature; also with 2-methyl and 2-phenyl derivatives 2: 83 percent / cyclohexane; diethyl ether / 0.03 h 3: 67 percent / iodine / aq. ethanol / 0.33 h View Scheme

pyridine

pyridine

pyridine 1 h; Ambient temperature;

sodium hydrogencarbonate; ethyl acetate

1: Et3N / toluene; tetrahydrofuran / 1 h / 45 °C 2: 65 percent / N-bromosuccinimide, H2O / dimethylsulfoxide / 0.17 h / 20 - 30 °C 3: H2O / ethanol / 3 h / Heating 5: 4.62 g / diethyl azodicarboxylate, Ph3P / tetrahydrofuran / 0.67 h 6: 3.45 g / H2 / 10percent Pd/C / ethanol / 1 h 7: 3.68 g / Na2CO3 / dimethylformamide / 1 h 8: 1.) sec-butyllithium, 2.) tosyl azide / 1.) cyclohexane, THF, -78 deg C, 15 min, 2.) cyclohexane, THF, RT, 1 h 9: 1.97 g / H2 / 10percent Pd/C / ethanol / 0.75 h / 2585.7 Torr 10: 1.26 g / t-BuOK / tetrahydrofuran / Ambient temperature 11: 0.48 g / H2 / 10percent Pd/C / ethanol / 18 h / 2585.7 Torr View Scheme