1: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 2: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 3: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 4: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux View Scheme

1: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 2: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 3: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 4: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 5: 95 percent / H2 / Pd/C / ethanol / 24 h 6: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C View Scheme

1: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 2: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 3: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 4: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 5: 95 percent / H2 / Pd/C / ethanol / 24 h 6: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 7: 90 percent / CrO3 / acetone / 0 °C View Scheme

[bis(2-methoxyethyl)amino]-sulfur trifluoride in dichloromethane