1.1: 90 percent / (-)-brucine / acetone; methanol / 0.5 h / 60 °C 2.1: 84 percent / N-hydroxysuccinimide; EDCI / CH2Cl2 3.1: p-TsCl; pyridine / 24 h / 80 °C 4.1: D2O / diethyl ether / 0.02 h / -78 °C 5.1: LDA / tetrahydrofuran / 0.02 h / -100 °C 5.2: D2O / diethyl ether View Scheme

in ethanol; water Ambient temperatureelectroreduction on mercury cathode;

1: 90 percent / (-)-brucine / acetone; methanol / 0.5 h / 60 °C 2: 84 percent / N-hydroxysuccinimide; EDCI / CH2Cl2 3: p-TsCl; pyridine / 24 h / 80 °C 4: n-BuLi / diethyl ether / 1 h / -100 °C View Scheme