Na naphthalenide in ethylene glycol dimethyl ether T=0 - 20°C; 6 h;

toluene-4-sulfonic acid in dichloromethane; water T=25°C; 95 h;

1: 93 percent / DCC, Et3N / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) 25 deg C, 23 h 2: 1.) H2, 2.) Et3N / 1.) 10percent Pd/C / 1.) CH3OH, 1 atm, 25 deg C, 3 h, 2.) 25 deg C, 16 h 3: 84 percent / CH2Cl2 / 50 h / 25 °C 4: 63 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 5: 25 percent / TsOH / CH2Cl2; H2O / 95 h / 25 °C View Scheme

1: 93 percent / DCC, Et3N / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) 25 deg C, 23 h 2: 1.) H2, 2.) Et3N / 1.) 10percent Pd/C / 1.) CH3OH, 1 atm, 25 deg C, 3 h, 2.) 25 deg C, 16 h 3: 84 percent / CH2Cl2 / 50 h / 25 °C 4: 63 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 5: 25 percent / TsOH / CH2Cl2; H2O / 95 h / 25 °C View Scheme

1: 1.) H2, 2.) Et3N / 1.) 10percent Pd/C / 1.) CH3OH, 1 atm, 25 deg C, 3 h, 2.) 25 deg C, 16 h 2: 84 percent / CH2Cl2 / 50 h / 25 °C 3: 63 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 4: 25 percent / TsOH / CH2Cl2; H2O / 95 h / 25 °C View Scheme

1: 84 percent / CH2Cl2 / 50 h / 25 °C 2: 63 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 3: 25 percent / TsOH / CH2Cl2; H2O / 95 h / 25 °C View Scheme

1: 63 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 2: 25 percent / TsOH / CH2Cl2; H2O / 95 h / 25 °C View Scheme

1: 88 percent 2: 82 percent / N-Methylmorpholin, Ethylchlorformiat / CH2Cl2 / 16 h / -15 - 20 °C 3: 76 percent / Naphthalin-Na / 1,2-dimethoxy-ethane / 6 h / 0 - 20 °C View Scheme

1: 82 percent / N-Methylmorpholin, Ethylchlorformiat / CH2Cl2 / 16 h / -15 - 20 °C 2: 76 percent / Naphthalin-Na / 1,2-dimethoxy-ethane / 6 h / 0 - 20 °C View Scheme

1: 88 percent 2: 82 percent / N-Methylmorpholin, Ethylchlorformiat / CH2Cl2 / 16 h / -15 - 20 °C 3: 76 percent / Naphthalin-Na / 1,2-dimethoxy-ethane / 6 h / 0 - 20 °C View Scheme