4-(1- 吡咯烷甲基)苯甲腈

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dissolve 4-(pyrrolidin-1-ylmethyl)-benzonitrile (918 mg, 4.93 mmol) in methanol (32 mL). Add cobalt(II) chloride hexahydrate (2.7 g, 9.87 mmol) and stir for 20 min. Cool the mixture to 0° C., and carefully add sodium borohydride (1.86 g, 49.3 mmol) in small batches. Stir the mixture for 1.5 h at room temperature. Quench the mixture with water and partition between water and chloroform. Extract the aqueous phase three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with a gradient of DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min) to give the title compound (421 mg, 45%). MS (ES+) m/z: 191 (M+H)+, Quench the mixture with water partition between water and chloroform Extract the aqueous phase three times with chloroform/iso-propanol (3:1) Dry the combined organic extracts over MgSO4 filter concentrate in vacuo Purify by chromatography on silica gel (80 g) eluting with a gradient of DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Add pyrrolidine (0.89 mL, 10.74 mmol) to a stirred solution of 4-bromomethyl-benzonitrile (1 g, 5.1 mmol) and triethylamine (1.5 mL, 10.74 mmol) in anhydrous THF (26 mL). Stir reaction overnight at room temperature. Partition the reaction mixture between EtOAc and water. Extract the aqueous phase twice with EtOAc. Dry the combined organic extracts over MgSO4, filter, and concentrate in vacuo to obtain the desired intermediate (918 mg, 97%) suitable for use without further purification. MS (APCI+) m/z: 187 (M+H)+. reaction overnight at room temperature Partition the reaction mixture between EtOAc and water Extract the aqueous phase twice with EtOAc Dry the combined organic extracts over MgSO4 filter concentrate in vacuo