methanol; N,N,N',N',N'',N''-hexamethylphosphoric triamide; samarium diiodide in tetrahydrofuran T=20 - 22°C; 12 h;

potassium hydroxide in methanol Heating;

1.1: aq. NaOH / ethanol 1.2: 28.7 g / aq. HCl 2.1: Brucine / acetone 2.2: aq. HCl 3.1: 84 percent / DOWEX X50-H(+) / methanol / 10 h / Heating 4.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 4.2: 78 percent Chromat. / diethyl ether / 1.58 h View Scheme

1.1: aq. NaOH / ethanol 1.2: 28.7 g / aq. HCl 2.1: Brucine / acetone 2.2: aq. HCl 3.1: 84 percent / DOWEX X50-H(+) / methanol / 10 h / Heating 4.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 4.2: 78 percent Chromat. / diethyl ether / 1.58 h 5.1: 60 percent / hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

1.1: aq. NaOH / ethanol 1.2: 28.7 g / aq. HCl 2.1: Brucine / acetone 2.2: aq. HCl 3.1: DOWEX X50-H(+) / methanol / 10 h / Heating 4.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 4.2: diethyl ether / 1.58 h View Scheme

1.1: aq. NaOH / ethanol 1.2: 28.7 g / aq. HCl 2.1: Brucine / acetone 2.2: aq. HCl 3.1: DOWEX X50-H(+) / methanol / 10 h / Heating 4.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 4.2: diethyl ether / 1.58 h 5.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 20 °C1.2: 29 percent / tetrahydrofuran / 20 °C2.1: 75 percent / sodium hydride / tetrahydrofuran / 20 °C