1: With hydrogen; Raney-Ni in tetrahydrofuran T=80°C; P=3000.3 Torr; 2: With sodium hydroxide in tetrahydrofuran; toluene 0.5 h;

sodium hydroxide in water T=10 - 60°C; pH=6.0 - 6.5;

sodium carbonate in dichloromethane; water T=-5 - 10°C;

1: With pyridine T=-10 - -5°C; 0.833333 h; 2: With triethylamine in ethyl acetate Heating; Further stages.;

hydrogen; propionic acid anhydride; platinum on activated charcoal in tetrahydrofuran T=60 - 70°C; P=7500.75 - 9000.9 Torr; Product distribution / selectivity;

1: With methanesulfonyl chloride in pyridine T=-10 - -5°C; 0.833333 h; 2: With sodium hydrogencarbonate in water; ethyl acetate T=-10 - 20°C; 0.5 h; 3: With triethylamine 0.666667 h; Heating / reflux;

1.1: NaH / tetrahydrofuran / 20 °C 1.2: tetrahydrofuran / 20 °C 2.1: H2; ethanolic NH3 / Raney-Co 3.1: Et3N / tetrahydrofuran / 0 °C 4.1: 86 percent / NaOAc; Br2 / 0 °C 5.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C 6.1: NaH / dimethylformamide / 0 °C 6.2: 96 percent / dimethylformamide / 0 °C 7.1: 80 percent / various solvent(s) / 200 - 205 °C 8.1: O3 / methanol / -78 °C 8.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C 9.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C 10.1: pyridine / 0.83 h / -10 - -5 °C 10.2: 86 percent / Et3N / ethyl acetate / Heating View Scheme

1.1: H2; ethanolic NH3 / Raney-Co 2.1: Et3N / tetrahydrofuran / 0 °C 3.1: 86 percent / NaOAc; Br2 / 0 °C 4.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C 5.1: NaH / dimethylformamide / 0 °C 5.2: 96 percent / dimethylformamide / 0 °C 6.1: 80 percent / various solvent(s) / 200 - 205 °C 7.1: O3 / methanol / -78 °C 7.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C 8.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C 9.1: pyridine / 0.83 h / -10 - -5 °C 9.2: 86 percent / Et3N / ethyl acetate / Heating View Scheme

1.1: Et3N / tetrahydrofuran / 0 °C 2.1: 86 percent / NaOAc; Br2 / 0 °C 3.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C 4.1: NaH / dimethylformamide / 0 °C 4.2: 96 percent / dimethylformamide / 0 °C 5.1: 80 percent / various solvent(s) / 200 - 205 °C 6.1: O3 / methanol / -78 °C 6.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C 7.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C 8.1: pyridine / 0.83 h / -10 - -5 °C 8.2: 86 percent / Et3N / ethyl acetate / Heating View Scheme

1.1: 86 percent / NaOAc; Br2 / 0 °C 2.1: 94 percent / BBr3 / CH2Cl2 / 0.67 h / -20 - 20 °C 3.1: NaH / dimethylformamide / 0 °C 3.2: 96 percent / dimethylformamide / 0 °C 4.1: 80 percent / various solvent(s) / 200 - 205 °C 5.1: O3 / methanol / -78 °C 5.2: 99 percent / NaBH4 / methanol / 1 h / -70 - 20 °C 6.1: 91 percent / Et3N; H2 / 10percent Pd/C/H2O / ethanol / 20 °C 7.1: pyridine / 0.83 h / -10 - -5 °C 7.2: 86 percent / Et3N / ethyl acetate / Heating View Scheme