t-BuLi in hexane; pentane addn. of t-BuLi in pentane at -100°C over 15 min to tropidine in pentane, further reacting at -80°C for 3 d, recooling to -100°C, addn. of Me3SnCl in hexane over 15 min, warming to room temp. over 1 h, stirring (30 min), add. of H2O; extn. (pentane), washing (brine), drying (Na2SO4), removal of solvents (reduced pressure), distn. (50°C/3E-3 Torr);

hydrogen; bis(bicyclo[2.2.1]hepta-2,5-diene)dichlorodirhodium; tri-cyclo-hexyl-phosphine in benzene T=100°C; P=60004.8 Torr; 6 h;

hydrogen; bis(bicyclo[2.2.1]hepta-2,5-diene)dichlorodirhodium; tributylphosphine in benzene T=100°C; P=60004.8 Torr; 6 h;

hydrogen; RhH(CO)(triphenylphosphine)3 in benzene T=100°C; P=60004.8 Torr; 6 h; various catalysts, formed in situ from various phosphines; Product distribution;

diethyl ether; platinum Hydrogenation;

Hydrogenation;

T=165°C;

T=165°C;

1: 86 percent / CH2Cl2 / 24 h / Ambient temperature 2: 40 percent / benzonitrile-hydrogen peroxide, phosphate buffer 3: 87 percent / lithium aluminium hydride / diethyl ether / 24 h View Scheme

1: 86 percent / CH2Cl2 / 24 h / Ambient temperature 2: 40 percent / benzonitrile-hydrogen peroxide, phosphate buffer 3: 87 percent / lithium aluminium hydride / diethyl ether / 24 h View Scheme