toluene-4-sulfonic acid in methanol T=60°C; 12 h;

1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 3: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 4: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 5: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min 7: 0.5 h / coproporphyrinogen-III oxidase (from Euglena gracilis) View Scheme

ueber mehrere Stufen;

1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 3: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 4: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 5: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

With  montmorillonite clay in  dichloromethane  

Multi-step reaction with 3 steps 1: 81.5 percent / acetic acid; H2O / 1 h / Heating2: 99 percent / H2 / 10percent Pd/C / tetrahydrofuran3: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C