tin; (S)-1-acetyl-N-tosylpyrrolidine-2-carboxamide in water; N,N-dimethyl-formamide T=20°C; 24 h; Overall yield = 83 percent; enantioselective reaction;

in diethyl ether T=-100°C; Addition; 1 h; Title compound not separated from byproducts;

1: 72 percent / indium / tetrahydrofuran; H2O / 12 h / 30 °C 2: 45 percent / Pseudomonas cepacia lipase immobilized on modified ceramic / tetrahydrofuran / 30 h / 24 °C 3: sodium hydroxide / methanol; H2O / 20 °C View Scheme

1: 45 percent / Pseudomonas cepacia lipase immobilized on modified ceramic / tetrahydrofuran / 30 h / 24 °C 2: sodium hydroxide / methanol; H2O / 20 °C View Scheme

in tetrahydrofuran T=-100°C; 1 h; Title compound not separated from byproducts.;

in diethyl ether T=-100°C; Title compound not separated from byproducts;

1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 2: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme

1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 2: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C 4: 0.21 g / K2CO3 / CH2Cl2 / 1 h / 20 °C 5: 0.15 g / LiAlH4 / tetrahydrofuran / 8 h / 20 °C View Scheme