sodium tetrahydroborate in ethylene glycol dimethyl ether; water T=-15°C; 0.00833333 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