1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C View Scheme

1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 3.1: Et3N / CH2Cl2 / 4 h / 0 °C 4.1: NaN3 / dimethylformamide / 75 °C 5.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme

1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 3.1: Et3N / CH2Cl2 / 4 h / 0 °C 4.1: NaN3 / dimethylformamide / 75 °C 5.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr 6.1: pyridine View Scheme

1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 3.1: Et3N / CH2Cl2 / 4 h / 0 °C 4.1: NaN3 / dimethylformamide / 75 °C View Scheme

1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 3.1: Et3N / CH2Cl2 / 4 h / 0 °C View Scheme