No renderable structure data available
CC(C)(C)OC(=O)N1CC(CC1CO)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 1334491-14-3 |
| Database ID | 56973583 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 4-fluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate (CAS 1334491-14-3) 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 56973583
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9334cd78dfcd45428df0eeb733d6bb72Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-12efe6db3e9a41f080a078497d010f1dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0dc4fc81c8774465b42ec0e77f76eb94Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of oxalyl chloride (0.28 ml, 2.3 mmol) in CH2Cl2 (20.0 ml) was added DMSO (0.39 ml) at −78° C. After 5 minutes, to the mixture was added 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (500 mg, 2.28 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 30 minutes at −78° C., and triethylamine (1.6 ml) was added The mixture was stirred for 30 minutes at −78° C., and stirred for 30 minutes at room temperature. Water was added to the mixture, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The crude product was used to the subsequent reaction without further purification. To a stirred solution of the crude product, methyl 4-aminobenzoate(302 mg, 2.0 mmol), and AcOH (0.13 ml) in DCE (10 ml) was added NaBH(OAc)3 (656 mg, 3.09 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. Sat. NaHCO3 was added to the residue, and extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3, v/v) as eluent to give methyl 4-(1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinyl)methylaminobenzoate (541 mg, 77%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.55-1.59 (m, 1H), 2.16-2.27 (m, 1H), 2.89-3.03 (m, 2H), 3.19-3.28 (m, 2H), 3.69-3.73 (m, 1H), 3.84 (s, 3H), 5.15 and 5.29 (each s, total 1H), 6.55-6.58 (m, 2H), 7.84-7.86 (m, 2H). was stirred for 30 minutes at −78° C. stirred for 30 minutes at room temperature extracted with CH2Cl2 The organic layer was dried over Na2SO4 concentrated in vacuo The crude product was used to the subsequent reaction without further purification The reaction mixture was stirred at room temperature for 18 hr The mixture was concentrated in vacuo Sat. NaHCO3 was added to the residue extracted with CH2Cl2 The extract was washed with brine dried over Na2SO4 concentrated in vacuo The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3
Source ID: ord-495bc24ae5f14500858c050e7dada5a0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF (1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.29-2.39 (m, 1H), 3.38-3.59 (m, 2H), 3.74-3.88 (m, 2H), 4.09-4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H). After cooled the mixture was concentrated in vacuo Water was added at 0° C., and extracted with EtOAc The extract was washed with water dried over Na2SO4 concentrated in vacuo
Source ID: ord-05ca194e27ec4ac792a5c4f80b2b5b5aConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of oxalyl chloride (0.28 ml, 2.3 mmol) in CH2Cl2 (20.0 ml) was added DMSO (0.39 ml) at −78° C. After 5 minutes, to the mixture was added 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (500 mg, 2.28 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 30 minutes at −78° C., and triethylamine (1.6 ml) was added. The mixture was stirred for 30 minutes at −78° C., and stirred for 30 minutes at room temperature. Water was added to the mixture, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The crude product was used to the subsequent reaction without further purification. To a stirred solution of the crude product, methyl 4-aminobenzoate(302 mg, 2.0 mmol), and AcOH (0.13 ml) in DCE (10 ml) was added NaBH(OAc)3 (656 mg, 3.09 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. Sat. NaHCO3 was added to the residue, and extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3, v/v) as eluent to give methyl 4-(1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinyl)methylaminobenzoate (541 mg, 77%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.55–1.59 (m, 1H), 2.16–2.27 (m, 1H), 2.89–3.03 (m, 2H), 3.19–3.28 (m, 2H), 3.69–3.73 (m, 1H), 3.84 (s, 3H), 5.15 and 5.29 (each s, total 1H), 6.55–6.58 (m, 2H), 7.84–7.86 (m, 2H). The mixture was stirred for 30 minutes at −78° C. stirred for 30 minutes at room temperature extracted with CH2Cl2 The organic layer was dried over Na2SO4 concentrated in vacuo The crude product was used to the subsequent reaction without further purification The reaction mixture was stirred at room temperature for 18 hr The mixture was concentrated in vacuo Sat. NaHCO3 was added to the residue extracted with CH2Cl2 The extract was washed with brine dried over Na2SO4 concentrated in vacuo The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3
Source ID: ord-f94de10be7b44ad0896ba87df3b7c455Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF(1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9H), 2.29–2.39 (m, 1H), 3.38–3.59 (m, 2H), 3.74–3.88 (m, 2H), 4.09–4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H). After cooled the mixture was concentrated in vacuo Water was added at 0° C., and extracted with EtOAc The extract was washed with water dried over Na2SO4 concentrated in vacuo
Source ID: ord-ee9b96ed53dd46be9218cbf162712a4cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9334cd78dfcd45428df0eeb733d6bb72Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of oxalyl chloride (0.28 ml, 2.3 mmol) in CH2Cl2 (20.0 ml) was added DMSO (0.39 ml) at −78° C. After 5 minutes, to the mixture was added 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (500 mg, 2.28 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 30 minutes at −78° C., and triethylamine (1.6 ml) was added The mixture was stirred for 30 minutes at −78° C., and stirred for 30 minutes at room temperature. Water was added to the mixture, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The crude product was used to the subsequent reaction without further purification. To a stirred solution of the crude product, methyl 4-aminobenzoate(302 mg, 2.0 mmol), and AcOH (0.13 ml) in DCE (10 ml) was added NaBH(OAc)3 (656 mg, 3.09 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. Sat. NaHCO3 was added to the residue, and extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3, v/v) as eluent to give methyl 4-(1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinyl)methylaminobenzoate (541 mg, 77%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.55-1.59 (m, 1H), 2.16-2.27 (m, 1H), 2.89-3.03 (m, 2H), 3.19-3.28 (m, 2H), 3.69-3.73 (m, 1H), 3.84 (s, 3H), 5.15 and 5.29 (each s, total 1H), 6.55-6.58 (m, 2H), 7.84-7.86 (m, 2H). was stirred for 30 minutes at −78° C. stirred for 30 minutes at room temperature extracted with CH2Cl2 The organic layer was dried over Na2SO4 concentrated in vacuo The crude product was used to the subsequent reaction without further purification The reaction mixture was stirred at room temperature for 18 hr The mixture was concentrated in vacuo Sat. NaHCO3 was added to the residue extracted with CH2Cl2 The extract was washed with brine dried over Na2SO4 concentrated in vacuo The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3
Source ID: ord-495bc24ae5f14500858c050e7dada5a0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF (1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.29-2.39 (m, 1H), 3.38-3.59 (m, 2H), 3.74-3.88 (m, 2H), 4.09-4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H). After cooled the mixture was concentrated in vacuo Water was added at 0° C., and extracted with EtOAc The extract was washed with water dried over Na2SO4 concentrated in vacuo
Source ID: ord-05ca194e27ec4ac792a5c4f80b2b5b5aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, 4.7 mmol) in THF (10.0 ml) was added BH3.THF (1.0 M solution in THF, 10.0 ml, 10.0 mmol) at 0° C. After stirred at room temperature for 1.0 h. After cooled, the mixture was concentrated in vacuo. Water was added thereto at 0° C., and extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (1.0 g, quant) as a a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.29-2.39 (m, 1H), 3.38-3.59 (m, 2H), 3.74-3.88 (m, 2H), 4.09-4.14 (m, 2H), 4.85 (m, 1H), 5.03 (br s, 1H), 5.16 (br s, 1H). After cooled the mixture was concentrated in vacuo Water was added at 0° C., and extracted with EtOAc The extract was washed with water dried over Na2SO4 concentrated in vacuo
Source ID: ord-05ca194e27ec4ac792a5c4f80b2b5b5aConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of oxalyl chloride (0.28 ml, 2.3 mmol) in CH2Cl2 (20.0 ml) was added DMSO (0.39 ml) at −78° C. After 5 minutes, to the mixture was added 1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinylmethanol (500 mg, 2.28 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 30 minutes at −78° C., and triethylamine (1.6 ml) was added. The mixture was stirred for 30 minutes at −78° C., and stirred for 30 minutes at room temperature. Water was added to the mixture, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and concentrated in vacuo. The crude product was used to the subsequent reaction without further purification. To a stirred solution of the crude product, methyl 4-aminobenzoate(302 mg, 2.0 mmol), and AcOH (0.13 ml) in DCE (10 ml) was added NaBH(OAc)3 (656 mg, 3.09 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. Sat. NaHCO3 was added to the residue, and extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3, v/v) as eluent to give methyl 4-(1-tert-butoxycarbonyl-4-fluoro-2-pyrrolidinyl)methylaminobenzoate (541 mg, 77%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.55–1.59 (m, 1H), 2.16–2.27 (m, 1H), 2.89–3.03 (m, 2H), 3.19–3.28 (m, 2H), 3.69–3.73 (m, 1H), 3.84 (s, 3H), 5.15 and 5.29 (each s, total 1H), 6.55–6.58 (m, 2H), 7.84–7.86 (m, 2H). The mixture was stirred for 30 minutes at −78° C. stirred for 30 minutes at room temperature extracted with CH2Cl2 The organic layer was dried over Na2SO4 concentrated in vacuo The crude product was used to the subsequent reaction without further purification The reaction mixture was stirred at room temperature for 18 hr The mixture was concentrated in vacuo Sat. NaHCO3 was added to the residue extracted with CH2Cl2 The extract was washed with brine dried over Na2SO4 concentrated in vacuo The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:3
Source ID: ord-f94de10be7b44ad0896ba87df3b7c455PubChem References
These sources are listed in the compound's public database record.
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