dicyclohexyl-carbodiimide in dichloromethane 1.) 0 deg C, 30 min, 2.) 25 deg C, 16 h;

1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / chloroform / 0 - 20 °C 3.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 3.2: 20 °C / Inert atmosphere; Cooling with ice 4.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 5.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

hydrogen; palladium on activated charcoal in methanol

1: (COCl)2; DMF / CH2Cl2 / 2 h / 20 °C 2: Na2CO3 / CH2Cl2; H2O / 2 h / 20 °C 3: 66 percent / POCl3 / dimethylformamide / 3 h / 20 °C 4: 62 percent / sodium hydrogen carbonate / acetonitrile / 18 h / Heating 5: hydrogen / Pd/C / ethyl acetate / 20 °C / 3878.61 Torr 6: NaH / tetrahydrofuran / 0 - 20 °C View Scheme

oxalyl dichloride in benzene

lithium aluminium tetrahydride

1.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 1 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / chloroform / 0 - 20 °C 3.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 3.2: 20 °C / Inert atmosphere; Cooling with ice 4.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 5.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

in benzene T=20°C;