chromium(VI) oxide in acetone T=0°C;

hydrogenchloride in methanol; water 72 h; Ambient temperature;

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

1: H2 / Pd/C / diethyl ether / 24 h 2: 90 percent / Et3N / CH2Cl2 / 0 - 4 °C / overnight 3: 90 percent / NaN3 / dimethylformamide / 70 °C / overnight 4: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 5: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 6: 95 percent / H2 / Pd/C / ethanol / 24 h 7: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 8: 90 percent / CrO3 / acetone / 0 °C View Scheme

1: 1.) H2, 2.) NaH / 1.) Pd/C / 1.) THF, 2 d, 2.) 0 deg C, 1 h, reflux, 3 h 2: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 3: 95 percent / H2 / Pd/C / ethanol / 24 h 4: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 5: 90 percent / CrO3 / acetone / 0 °C View Scheme

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

1: 90 percent / LAH / tetrahydrofuran / 0 deg C to reflux 2: 95 percent / H2 / Pd/C / ethanol / 24 h 3: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 4: 90 percent / CrO3 / acetone / 0 °C View Scheme

1: 95 percent / H2 / Pd/C / ethanol / 24 h 2: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 3: 90 percent / CrO3 / acetone / 0 °C View Scheme

ethylenediaminetetraacetic acid in phosphate buffer T=30°C; pH=8.00; 18 h; Title compound not separated from byproducts.;

1: 90 percent / aq. K2CO3 / tetrahydrofuran / 4 h / 0 °C 2: 90 percent / CrO3 / acetone / 0 °C View Scheme