hydrazine hydrate in ethanol 0.5 h; Heating;

1.1: K2CO3; Adogen / toluene / 20 - 90 °C 2.1: LDA / tetrahydrofuran / -60 - 0 °C 2.2: tetrahydrofuran / 18 h / -60 - 20 °C 3.1: aq. NaOH / ethanol 3.2: 28.7 g / aq. HCl 4.1: Brucine / acetone 4.2: aq. HCl 5.1: DOWEX X50-H(+) / methanol / 10 h / Heating 6.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 6.2: diethyl ether / 1.58 h 7.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

1.1: LDA / tetrahydrofuran / -60 - 0 °C 1.2: tetrahydrofuran / 18 h / -60 - 20 °C 2.1: aq. NaOH / ethanol 2.2: 28.7 g / aq. HCl 3.1: Brucine / acetone 3.2: aq. HCl 4.1: DOWEX X50-H(+) / methanol / 10 h / Heating 5.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 5.2: diethyl ether / 1.58 h 6.1: 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 5.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

1.1: Brucine / acetone 1.2: aq. HCl 2.1: DOWEX X50-H(+) / methanol / 10 h / Heating 3.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 3.2: diethyl ether / 1.58 h 4.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

1.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 1.2: diethyl ether / 1.58 h 2.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme

1.1: DOWEX X50-H(+) / methanol / 10 h / Heating 2.1: sodium hydride / diethyl ether / 1.5 h / 25 °C 2.2: diethyl ether / 1.58 h 3.1: hydrazine monohydrate / ethanol / 0.5 h / Heating View Scheme