tert-butyl 2-phenylpyrrolidine-1-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield). The reaction mixture was then quenched with aqueous NH4Cl (20 mL) diluted with Et2O (150 mL) the layers were separated the aqueous layer was extracted twice with Et2O The combined organic phases were washed with H2O and brine dried (MgSO4) filtered concentrated The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)