hydrogenchloride T=20°C; Hydrolysis;

1.1: 99 percent / NH4OAc / 1 h / Heating 2.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3.1: ethanol / 25 °C 3.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 4.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 5.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 6.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 7.1: 99 percent / various solvent(s) / 20 h / 230 °C 8.1: Chiracel OD / propan-2-ol; hexane 9.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 10.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 11.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 12.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 13.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 14.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 15.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 16.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 17.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 18.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1.1: POCl3 / 0.75 h / 35 °C 1.2: 99 percent / aq. NaOH / dimethylformamide / 0.17 h / Heating 2.1: 99 percent / NH4OAc / 1 h / Heating 3.1: 96 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4.1: ethanol / 25 °C 4.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 5.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 6.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 7.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 8.1: 99 percent / various solvent(s) / 20 h / 230 °C 9.1: Chiracel OD / propan-2-ol; hexane 10.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 11.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 12.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 13.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 14.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 15.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 16.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 17.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 18.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 19.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1.1: ethanol / 25 °C 1.2: 64 percent / N2H4*H2O / ethanol / 5 h / Heating 2.1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 3.1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 4.1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 5.1: 99 percent / various solvent(s) / 20 h / 230 °C 6.1: Chiracel OD / propan-2-ol; hexane 7.1: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 8.1: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 9.1: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 10.1: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 11.1: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 12.1: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 13.1: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 14.1: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 15.1: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 16.1: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

aluminium trichloride; bis(2-methoxyethoxy)aluminum hydride in tetrahydrofuran

1: 79 percent / AcOH / tetrahydrofuran / 35 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1: 61 percent / EDCI; DMAP / CH2Cl2 / 19 h / 25 °C 2: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 3: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 4: 99 percent / various solvent(s) / 20 h / 230 °C 5: Chiracel OD / propan-2-ol; hexane 6: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 7: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 8: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 9: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 10: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 11: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 12: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 13: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 14: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 15: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 2: 99 percent / various solvent(s) / 20 h / 230 °C 3: Chiracel OD / propan-2-ol; hexane 4: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 5: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 6: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 7: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 8: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 9: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 10: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 11: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 12: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 13: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1: 67 percent / p-toluenesulfonyl chloride; Et3N / CH2Cl2 / 20 h / 25 °C 2: 88 percent / EDCI; DMAP / CH2Cl2 / 20 °C 3: 99 percent / various solvent(s) / 20 h / 230 °C 4: Chiracel OD / propan-2-ol; hexane 5: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 6: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 7: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 8: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 9: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 10: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 11: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 12: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 13: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 14: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme

1: 99 percent / various solvent(s) / 20 h / 230 °C 2: Chiracel OD / propan-2-ol; hexane 3: bis(trimethylsilyl)peroxide; LDA / tetrahydrofuran / 4 h / -40 °C 4: 27.9 mg / tetrahydrofuran / 2 h / -40 - 20 °C 5: 90 percent / H2 / Pd/C / methanol / 17 h / 25 °C / atmospheric pressure 6: 69 percent / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 0 - 25 °C 7: 69 percent / Lawesson's reagent / toluene / 4 h / Heating 8: 61 percent / Raney Ni / tetrahydrofuran / 2 h / 25 °C 9: 82 percent / H2; aq. HCl / PtO2 / methanol / 2 h / 25 °C / 2068.59 - 2327.17 Torr 10: 98 percent / Bu4NF / tetrahydrofuran / 0 - 25 °C 11: 62 percent / PPh3 / acetonitrile; CCl4 / 1 h / 70 °C 12: 43 percent / AlCl3; bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran View Scheme