1: 80 percent / pyridine / 38 °C 2: 1.) CH3CH=C(CH3)2, NaOCl2-NaH2PO4, 2.) (i-Pr)2NEt / 1.) t-BuOH, H2O; 2.) CH2Cl2 3: 75 percent / NaBH4 / tetrahydrofuran; various solvent(s) View Scheme

2: 99 percent / RuO4 / CH2Cl2; CCl4 3: NaH / 1,2-dimethoxy-ethane 4: 1.) p-TSOH, AC2O, 2.) K2CO3 / 2.) benzene 5: 80 percent / pyridine / 38 °C 6: 1.) CH3CH=C(CH3)2, NaOCl2-NaH2PO4, 2.) (i-Pr)2NEt / 1.) t-BuOH, H2O; 2.) CH2Cl2 7: 75 percent / NaBH4 / tetrahydrofuran; various solvent(s) View Scheme

1: 75 percent / NaBH4 / tetrahydrofuran; various solvent(s) View Scheme

Yield given. Multistep reaction;

1: 98 percent / NaH / dimethylformamide / 2 h / Ambient temperature 2: 96 percent / sodium borohydride / ethanol / Ambient temperature 3: 1) dimethyl sulfoxide, oxalyl dichloride; 3) triethylamine / 1) CH2Cl2, -60 deg C, 5 min; 2) CH2Cl2, -60 deg C, 15 min; 3) CH2Cl2, -60 deg C, 10 min, then room temp. 4: 100 percent / triphenylphosphine, diethyl azodicarboxylate / dimethylformamide / Ambient temperature 5: 1.) hydrazine, 2.) pyridine / 1.) methanol, 30 deg C, 1 d, 2.) RT, overnight 6: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 99 percent / RuO4 / CCl4; CH2Cl2 / 1 h / Ambient temperature 8: 99.6 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature 9: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K2CO3 / 1.) RT, overnight, 2.) benzene, RT, overnight 10: pyridine / 168 h / 38 °C 11: aq. NaClO2, aq. NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature 12: N,N-diisopropylethylamine / CH2Cl2 / 1 h / Ambient temperature 13: 76 percent / NaBH4 / tetrahydrofuran; various solvent(s) / 3 h / Ambient temperature 14: 75 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 15: 95 percent / H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 16: 94 percent / 1 M aq. HCl / 1 h / Ambient temperature View Scheme

hydrogenchloride 1 h; Ambient temperature;

1: N,N-diisopropylethylamine / CH2Cl2 / 1 h / Ambient temperature 2: 76 percent / NaBH4 / tetrahydrofuran; various solvent(s) / 3 h / Ambient temperature 3: 75 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 4: 95 percent / H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 5: 94 percent / 1 M aq. HCl / 1 h / Ambient temperature View Scheme

1: 95 percent / H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 2: 94 percent / 1 M aq. HCl / 1 h / Ambient temperature View Scheme

1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 2: 99 percent / RuO4 / CCl4; CH2Cl2 / 1 h / Ambient temperature 3: 99.6 percent / NaH / 1,2-dimethoxy-ethane / 2 h / Ambient temperature 4: 1.) acetic anhydride, p-toluenesulfonic acid, 2.) K2CO3 / 1.) RT, overnight, 2.) benzene, RT, overnight 5: pyridine / 168 h / 38 °C 6: aq. NaClO2, aq. NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s) / 24 h / Ambient temperature 7: N,N-diisopropylethylamine / CH2Cl2 / 1 h / Ambient temperature 8: 76 percent / NaBH4 / tetrahydrofuran; various solvent(s) / 3 h / Ambient temperature 9: 75 percent / pyridinium dichromate / dimethylformamide / Ambient temperature 10: 95 percent / H2 / 5percent Pd/C / methanol / 1 h / Ambient temperature 11: 94 percent / 1 M aq. HCl / 1 h / Ambient temperature View Scheme