formic acid; palladium on activated charcoal in methanol 2.5 h; Yield given;

1: 92.5 percent / N-methylmorpholine / CH2Cl2 / 2 h 2: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H2O / 6 h 3: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C 4: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C 5: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 6: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 7: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 8: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: N-methylmorpholine / CH2Cl2 / 0.17 h / -5 °C 2: 92.5 percent / N-methylmorpholine / CH2Cl2 / 2 h 3: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H2O / 6 h 4: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C 5: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C 6: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 7: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 8: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 9: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: 92.5 percent / N-methylmorpholine / CH2Cl2 / 2 h 2: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H2O / 6 h 3: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C 4: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C 5: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 6: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 7: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 8: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C 2: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C 3: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 4: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 5: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 6: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H2O / 6 h 2: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C 3: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C 4: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 5: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 6: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 7: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: 2.5 N NaOH / tetrahydrofuran; H2O / 6 h 2: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 3: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 4: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: HCl(gas) / ethyl acetate / 0.75 h / 0 °C 2: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 3: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

1: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO3 / dimethylformamide / 72 h / 0 - 5 °C 2: HCOOH / 10percent Pd/C / methanol / 2.5 h View Scheme

Multistep reaction;