No renderable structure data available
CC(C)(C)OC(=O)N1CCCC1C2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 2-phenylpyrrolidine-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 154874-88-1 |
| Database ID | 3772557 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 2-phenylpyrrolidine-1-carboxylate (CAS 154874-88-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 3772557
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-84affd3848bc4f158cc0abf555ed74b2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-14bd27733a164910a2ebc08fa2747b84Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-f7cffdb1601b4147957e2c4ae980b705Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-14bd27733a164910a2ebc08fa2747b84Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-14bd27733a164910a2ebc08fa2747b84Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-f7cffdb1601b4147957e2c4ae980b705Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-f7cffdb1601b4147957e2c4ae980b705Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-84affd3848bc4f158cc0abf555ed74b2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-14bd27733a164910a2ebc08fa2747b84Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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)
Source ID: ord-f7cffdb1601b4147957e2c4ae980b705PubChem References
These sources are listed in the compound's public database record.
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