1: 94 percent / 2,2-dimethoxypropane / Heating; * 2: 71 percent / NaH / tetrahydrofuran / 2 h / Heating 3: 97 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 4: 93 percent / celite / benzene / 4 h / porcine pancreatic lipase 5: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 6: 84 percent / dimethylsulfoxide / 12 h / 45 °C 7: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 8: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 9: 82 percent / NaN3 / dimethylformamide / 40 °C 10: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 11: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

1: 71 percent / NaH / tetrahydrofuran / 2 h / Heating 2: 97 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 3: 93 percent / celite / benzene / 4 h / porcine pancreatic lipase 4: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 5: 84 percent / dimethylsulfoxide / 12 h / 45 °C 6: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 7: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 8: 82 percent / NaN3 / dimethylformamide / 40 °C 9: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 10: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

1: 95 percent / Dowex-WX4 / various solvent(s) / Heating 2: 85 percent / Na, MeOH / tetrahydrofuran / 1.5 h / Heating 3: 79 percent / aq. NaCl / dimethylsulfoxide / 4 h / Heating 4: 85 percent / Triton-X, 0.1 M aq. NaOH / 30 h / α-chymotrypsin 5: 1.) ethyl chloroformate, triethylamine, 2.) aq. NaN3 / 1.) acetone, from 0 deg C to 25 deg C, 55 min, 2.) acetone, 0 deg C, 2 h 6: toluene / 8 h / Heating 7: 6 N aq. HCl / 2 h / Heating View Scheme

1: 97 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 2: 93 percent / celite / benzene / 4 h / porcine pancreatic lipase 3: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 4: 84 percent / dimethylsulfoxide / 12 h / 45 °C 5: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 6: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 7: 82 percent / NaN3 / dimethylformamide / 40 °C 8: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 9: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

1: 93 percent / celite / benzene / 4 h / porcine pancreatic lipase 2: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 3: 84 percent / dimethylsulfoxide / 12 h / 45 °C 4: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 5: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 6: 82 percent / NaN3 / dimethylformamide / 40 °C 7: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 8: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

1: 85 percent / Triton-X, 0.1 M aq. NaOH / 30 h / α-chymotrypsin 2: 1.) ethyl chloroformate, triethylamine, 2.) aq. NaN3 / 1.) acetone, from 0 deg C to 25 deg C, 55 min, 2.) acetone, 0 deg C, 2 h 3: toluene / 8 h / Heating 4: 6 N aq. HCl / 2 h / Heating View Scheme

1: 79 percent / aq. NaCl / dimethylsulfoxide / 4 h / Heating 2: 85 percent / Triton-X, 0.1 M aq. NaOH / 30 h / α-chymotrypsin 3: 1.) ethyl chloroformate, triethylamine, 2.) aq. NaN3 / 1.) acetone, from 0 deg C to 25 deg C, 55 min, 2.) acetone, 0 deg C, 2 h 4: toluene / 8 h / Heating 5: 6 N aq. HCl / 2 h / Heating View Scheme

1: 1.) ethyl chloroformate, triethylamine, 2.) aq. NaN3 / 1.) acetone, from 0 deg C to 25 deg C, 55 min, 2.) acetone, 0 deg C, 2 h 2: toluene / 8 h / Heating 3: 6 N aq. HCl / 2 h / Heating View Scheme

1: 93 percent / triethylamine / tetrahydrofuran / 3 h / 0 - 25 °C 2: 84 percent / dimethylsulfoxide / 12 h / 45 °C 3: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 4: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 5: 82 percent / NaN3 / dimethylformamide / 40 °C 6: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 7: 6 N aq. HCl / 18 h / Ambient temperature View Scheme

1: 77 percent / 0.1 N aq. NaOH / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 2: 91 percent / triethylamine / tetrahydrofuran / 2 h / 0 - 25 °C 3: 82 percent / NaN3 / dimethylformamide / 40 °C 4: 1.) triphenylphosphine, 2.) H2O / 1.)THF, RT, 3 h, 2.) THF, RT, 3h 5: 6 N aq. HCl / 18 h / Ambient temperature View Scheme