1: D-prolinol With sodium hydrogencarbonate in water; ethyl acetate 0.0833333 h; 2: benzyl chloroformate in water; ethyl acetate 5 h;

1: With dimethylsulfide borane complex in tetrahydrofuran 2 h; Heating / reflux; 2: With hydrogenchloride; water in tetrahydrofuran T=0°C;

in 1,4-dioxane; water T=25°C; 24 h;

sodium tetrahydroborate in methanol 0.5 h;

sodium tetrahydroborate; lithium chloride

1: 91 percent / NaN3 / dimethylformamide / 12 h / 100 °C 2: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 3: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 4: 82 percent / NaHCO3 / aq. ethanol 5: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 6: 79 percent / aq. NaIO4 / methanol / 2 h 7: 88 percent / NaBH4 / methanol / 0.5 h View Scheme

1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 2: 82 percent / NaHCO3 / aq. ethanol 3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 4: 79 percent / aq. NaIO4 / methanol / 2 h 5: 88 percent / NaBH4 / methanol / 0.5 h View Scheme

1: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C 2: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature 3: 82 percent / NaHCO3 / aq. ethanol 4: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature 5: 79 percent / aq. NaIO4 / methanol / 2 h 6: 88 percent / NaBH4 / methanol / 0.5 h View Scheme

1: 46 percent / Candida antarctica lipase / aq. phosphate buffer / 38 h / 30 °C 2: 97 percent / NaBH4; LiCl View Scheme

1: 98 percent / K2CO3 / dimethylformamide / 20 °C 2: 46 percent / Candida antarctica lipase / aq. phosphate buffer / 38 h / 30 °C 3: 97 percent / NaBH4; LiCl View Scheme