1: 94 percent / DCC; DMAP / CH2Cl2 2: 84 percent / LiOH / tetrahydrofuran; H2O View Scheme

1: Et3N / tetrahydrofuran / 0.5 h / -10 °C 2: NaBH4 / H2O; tetrahydrofuran / 4 h / Ambient temperature 3: pyridine / -5 °C 4: NaI / acetone / 4 h / Heating 5: tetrahydrofuran / 0.17 h / -50 °C 6: 2N NaOH / dioxane; H2O / Ambient temperature View Scheme

1.1: dicyclohexyl-carbodiimide / dichloromethane / 41 h / -10 - 0 °C 2.1: hydrogenchloride / 1,4-dioxane; methanol / 3.25 h / 10 - 15 °C / Industry scale 3.1: sodium hydrogencarbonate / acetonitrile / 4.17 h / 15 - 20 °C / Industry scale 4.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 3.25 h / -18 - 0 °C / Inert atmosphere; Industry scale 4.2: 2.75 h / -5 - 0 °C / Industry scale 5.1: n-heptane; tetrahydrofuran; ethylbenzene / 42.83 h / -2 - 20 °C 5.2: Industry scale 6.1: Dess-Martin periodane / butanone / 30 - 43 °C View Scheme

1: With 4-methyl-morpholine; chloroformic acid ethyl ester in tetrahydrofuran T=-10°C; 0.166667 h; 2: With sodium tetrahydroborate in methanol T=0°C; 0.333333 h; Further stages.;

1: 68.5 percent / EEDQ / diethyl ether / 2 h 2: 91.4 percent / HCl (gas) / acetic acid / 3 h 3: 100 percent / Et3N / methanol / 15 h / Heating 4: 100 percent / aq. Ba(OH)2 / methanol / 15 h View Scheme

1.1: Boc2O; DMAP 2.1: NaOH / methanol; H2O 3.1: ClCOOEt; NMO 3.2: NaBH4 / methanol 3.3: 81 percent / CBr4; PPh3 View Scheme

1: DCC / ethyl acetate / 1.) 0 deg C, 2.) 3 h, room temperature 2: NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 3: 92 percent / imidazole / dimethylformamide / 3 h / Ambient temperature View Scheme

Multistep reaction;