1.1: NaI; Na2CO3 / dimethylformamide / 65 °C 2.1: aq. NaHCO3 / acetone 3.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C 4.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 4.2: NaBH4 / methanol 4.3: 86 percent / CuSO4 / methanol 5.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 6.1: Et3N / CH2Cl2 / 4 h / 0 °C 7.1: NaN3 / dimethylformamide / 75 °C View Scheme

potassium carbonate in acetone T=20°C;

N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate in N,N-dimethyl-formamide T=80°C; 12 h;

1: methanol 2: N,N-dimethyl-formamide 3: dichloromethane View Scheme

1: N,N-dimethyl-formamide 2: dichloromethane View Scheme

1.1: NaI; Na2CO3 / dimethylformamide / 65 °C 2.1: aq. NaHCO3 / acetone 3.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C 4.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 4.2: NaBH4 / methanol 4.3: 86 percent / CuSO4 / methanol 5.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 6.1: Et3N / CH2Cl2 / 4 h / 0 °C View Scheme

in N,N-dimethyl-formamide 5 h; Heating / reflux; Product distribution / selectivity;

1: methanol 2: N,N-dimethyl-formamide View Scheme

sodium tris(acetoxy)borohydride in dichloromethane 18 h;

sodium carbonate in dichloromethane T=5 - 25°C;