1.1: sodium hydroxide / chloroform / 0 - 20 °C 2.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 2.2: 20 °C / Inert atmosphere; Cooling with ice 3.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 4.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

sodium hydroxide; ammonia; benzaldehyde in N-methyl-acetamide; methanol; 2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamide oxalate; ethanol; dichloromethane; toluene

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; Inert atmosphereReflux;

1: 90 percent / ammonium acetate / acetic acid / 1.5 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 78 percent / 1 h / Heating 4: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

1: 78 percent / 1 h / Heating 2: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

borane-THF; boron trifluoride diethyl etherate in tetrahydrofuran 2 h; Heating;

1: LiAlH4 / tetrahydrofuran / 3 h / Heating 2: 78 percent / 1 h / Heating 3: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

1: 96 percent / K2CO3 / CHCl3; methanol / 4 h / Heating 2: 90 percent / ammonium acetate / acetic acid / 1.5 h / Heating 3: LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 78 percent / 1 h / Heating 5: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

1: 96 percent / K2CO3 / CHCl3; methanol / 4 h / Heating 2: 90 percent / ammonium acetate / acetic acid / 1.5 h / Heating 3: LiAlH4 / tetrahydrofuran / 3 h / Heating 4: 78 percent / 1 h / Heating 5: BF3*OEt2; BH3*THF / tetrahydrofuran / 2 h / Heating View Scheme

T=50 - 60°C; und Behandeln des entstandenen Jodmethylats mit feuchtem Alkohol;