1: 100 percent / NaOAc; AcOH; NH2OH*HCl / 18 h / 130 °C 2: 76 percent / HNO3; AcOH / 20 h / 20 °C 3: 84 percent / aq. Na2S2O4; Bu4NCl / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: ammonium acetate / acetic acid / 5 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere; Reflux 3.1: triethylamine / dichloromethane / 3 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux 5.1: sodium hydroxide / chloroform / 0 - 20 °C 6.1: trichlorophosphate / acetonitrile / 3 h / Reflux; Inert atmosphere 6.2: 20 °C / Inert atmosphere; Cooling with ice 7.1: palladium 10 on activated carbon; hydrogen; acetic acid / methanol / 16 h 8.1: berberine bridge enzyme; tris(hydroxymethyl)methylamine hydrochloride; magnesium chloride / toluene / 24 h / 40 °C / pH 9 / Darkness; Enzymatic reaction View Scheme

1: NaBH4 / methanol 2: PBr3 / diethyl ether 3: (i) nBuLi, THF, (ii) /BRN= 2130929/, (iii) aq. NaIO4, MeOH View Scheme

bromine; sodium acetate in acetic acid T=40°C; 11 h;

pyridinium hydrobromide perbromide in methanol 1.) 0 deg C, 1 h, 2.) r.t., 1 h;

1: (i) aq. HCl, dioxane, (ii) /BRN= 385737/, Py 2: HCl 3: LiAlH4 / tetrahydrofuran 4: H2 / Pd-C / ethanol View Scheme

1: 90 percent / ammonium acetate / acetic acid / 1.5 h / Heating 2: LiAlH4 / tetrahydrofuran / 3 h / Heating 3: 78 percent / 1 h / Heating View Scheme

hydroxylamine hydrochloride; sodium acetate; acetic acid T=130°C; 18 h;

hydroxylamine hydrochloride; Titanium(IV) oxide 0.0833333 h; Microwave irradiationNeat (no solvent);