1: sodium tetrahydroborate / methanol / 20 - 70 °C / Inert atmosphere 2: THF-d8 (tetrahydrofuran-d8) / 600 h / phosphate buffer in D2O 3: THF-d8 (tetrahydrofuran-d8) / 600 h / phosphate buffer in D2O 4: THF-d8 (tetrahydrofuran-d8) / 240 h / phosphate buffer in D2O View Scheme

1: H2 / 10percent Pd/C / ethanol / 24 h / 45 °C / 760 Torr 2: 64 percent / ethanol View Scheme

(i) AcOEt, (ii) H2O, (iii) aq. NaOH; Multistep reaction;

sodium tetrahydroborate in ethanol

1: sodium tetrahydroborate / methanol / 20 - 70 °C / Inert atmosphere 2: THF-d8 (tetrahydrofuran-d8) / 600 h / phosphate buffer in D2O 3: THF-d8 (tetrahydrofuran-d8) / 600 h / phosphate buffer in D2O 4: THF-d8 (tetrahydrofuran-d8) / 264 h / phosphate buffer in D2O View Scheme