1: With 4-methyl-morpholine; isobutyl chloroformate in tetrahydrofuran 0.333333 h; Inert atmosphereCooling with ice; 2: With sodium tetrahydroborate; water in tetrahydrofuran 1 h; Cooling with ice;

1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in diethyl ether T=-78°C; 4.16667 h; 2: oxirane With boron trifluoride diethyl etherate in diethyl ether T=-78°C; 0.5 h;

1: With lithium borohydride in tetrahydrofuran T=50°C; 3 h; Inert atmosphere; 2: With hydrogenchloride in water pH=2 - 3;

1: With benzoic acid in chloroform T=-50°C; aza-Michael addition; 22 h; 2: With sodium tetrahydroborate in methanol; chloroform T=0°C; 0.5 h; Further stages. Title compound not separated from byproducts.;

1: N-Boc-pyrrolidine With sec.-butyllithium; (-)-sparteine in diethyl ether T=-78°C; 4 h; 2: oxirane With boron trifluoride diethyl etherate in diethyl ether T=-78°C; 2.5 h; Title compound not separated from byproducts;

1: N-methylmorpholine-N-oxide / tetra-n-propylammonium perruthenate / CH2Cl2 / 3.5 h / 20 °C 2: 907 mg / tetrahydrofuran / 3 h 3: tetrahydrofuran / 5 h / 20 °C 4: 868 mg / Na2BO3*4H2O; water / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: Et3N / tetrahydrofuran; diethyl ether / 1 h / 0 °C 2.1: diethyl ether / 3 h / 0 °C 2.2: AgOBz; Et3N / 3 h / 0 - 20 °C 3.1: LiAlH4 / diethyl ether / 0.5 h / 0 °C View Scheme

1: 907 mg / tetrahydrofuran / 3 h 2: tetrahydrofuran / 5 h / 20 °C 3: 868 mg / Na2BO3*4H2O; water / tetrahydrofuran / 18 h / 20 °C View Scheme

1: tetrahydrofuran / 5 h / 20 °C 2: 868 mg / Na2BO3*4H2O; water / tetrahydrofuran / 18 h / 20 °C View Scheme

1.1: sodium hydroxide / tetrahydrofuran; water / 20 °C 1.2: pH 2 - 3 2.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere 3.1: potassium hydroxide / diethyl ether; diethylene glycol monoethyl ether; water / 0.5 h / Heating 3.2: 20 °C / Cooling with ice 4.1: silver benzoate; triethylamine / 0 °C / Inert atmosphere; Darkness 5.1: lithium borohydride / tetrahydrofuran / 3 h / 50 °C / Inert atmosphere 5.2: pH 2 - 3 View Scheme