No renderable structure data available
CC(C)(C)OC(=O)N1CC(CC1CO)(F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl 4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 317354-91-9 |
| Database ID | 22001352 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl 4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate (CAS 317354-91-9) 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 22001352
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-b698f1e546dd4d51836eb86c444a9504Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f4ee8a04fad94df1b4df5aa23050a50fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (600 mg, 2.53 mmol), methyl 4-hydroxybenzoate (462 mg, 3.03 mmol), Ph3P (795 mg, 3.03 mmol) in THF (10 ml) was added DIAD (597 ul, 3.03 mmol) at room temperature. The mixture was heated at reflux for 3 h with stirring. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (831 mg, 88%) as a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9 H), 2.53-2.61 (m, 2 H), 3.63-4.41 (series of m, total 8 H), 6.94 (d, J=8.8 Hz, 2 H), 7.99 (d, J=8.8 Hz, 2 H). The mixture was heated at reflux for 3 h The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-2e0650f0343940eca49601f57dc349ccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of N-(tert-butoxycarbonyl) 4,4-difluoroproline (3.00 g, 11.9 mmol) in THF (20 ml) was added BH3.DMS (1.1 ml, 11.9 mmol) at room temperature. The mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was quenched by the addition of H2O (100 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 75%) as a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9 H), 2.04-2.55 (m, 2 H), 3.59-4.17 (m, 5 H). at room temperature The mixture was heated at reflux for 2 h The residue was quenched by the addition of H2O (100 ml) extracted with CHCl3 (2×200 ml) The combined extracts were dried over MgSO4 evaporated The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent
Source ID: ord-9f77c9a8aa9348f6bc1a65f05cb78ba1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 8.89 mmol), Et3N (6.2 ml, 44.5 mmol), DMSO (6.3 ml, 88.9 mmol) in CH2Cl2 (20 ml) was added SO3-pyridine (4.25 g, 26.7 mmol). After 3 h stirring, the mixture was concentrated in vacuo and diluted with Et2O (200 ml). The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarbaldehyde (1.40 g, 67%) as a yellow oil. 1H-NMR (CDCl3) δ1.45-1.52 (m, 9 H), 2.49 (m, 2 H), 3.75-3.88 (m, 2 H), 4.29-4.42 (m, 1 H), 9.54 and 9.60 (s, each, total 1 H). the mixture was concentrated in vacuo diluted with Et2O (200 ml) The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml) dried over MgSO4 concentrated in vacuo The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-e5557662dca544ac8e5c4666f7854951Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4difluoro-2-pyrrolidinylmethanol (600 mg, 2.53 mmol), methyl 4-hydroxybenzoate (462 mg, 3.03 mmol), Ph3P (795 mg, 3.03 mmol) in THF (10 ml) was added DIAD (597 ul, 3.03 mmol) at room temperature. The mixture was heated at reflux for 3 h with stirring. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (831 mg, 88%) as a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 2.53–2.61 (m, 2 H), 3.63–4.41 (series of m, total 8 H), 6.94 (d, J=8.8 Hz, 2H), 7.99(d, J=8.8 Hz, 2H). The mixture was heated at reflux for 3 h The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-b5b8c9b3af584504b4cd88d3d79147c4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of N-(tert-butoxycarbonyl) 4,4-difluoroproline (3.00 g, 11.9 mmol) in THF (20 ml) was added BH3.DMS (1. 1 ml, 11.9 mmol) at room temperature. The mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was quenched by the addition of H2O (100 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 75%) as a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 2.04–2.55 (m, 2 H), 3.59–4.17 (m, 5 H). at room temperature The mixture was heated at reflux for 2 h The residue was quenched by the addition of H2O (100 ml) extracted with CHCl3 (2×200 ml) The combined extracts were dried over MgSO4 evaporated The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent
Source ID: ord-bb5d5825beea47409329f47aa7eae666Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 8.89 mmol), Et3 N (6.2 ml, 44.5 mmol), DMSO (6.3 ml, 88.9 mmol) in CH2Cl2 (20 ml) was added SO3 pyridine (4.25 g, 26.7 mmol). After 3 h stirring, the mixture was concentrated in vacuo and diluted with Et2O (200 ml). The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarbaldehyde (1.40 g, 67%) as a yellow oil. 1H-NMR (CDCl3) δ 1.45–1.52 (m, 9 H), 2.49 (m, 2 H), 3.75–3.88 (m, 2 H), 4.29–4.42 (m, 1 H), 9.54 and 9.60 (s, each, total 1 H). the mixture was concentrated in vacuo diluted with Et2O (200 ml) The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml) dried over MgSO4 concentrated in vacuo The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-9d04513045dc49d2a40be4e9ce361ca8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (600 mg, 2.53 mmol), methyl 4-hydroxybenzoate (462 mg, 3.03 mmol), Ph3P (795 mg, 3.03 mmol) in THF (10 ml) was added DIAD (597 ul, 3.03 mmol) at room temperature. The mixture was heated at reflux for 3 h with stirring. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (831 mg, 88%) as a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9 H), 2.53-2.61 (m, 2 H), 3.63-4.41 (series of m, total 8 H), 6.94 (d, J=8.8 Hz, 2 H), 7.99 (d, J=8.8 Hz, 2 H). The mixture was heated at reflux for 3 h The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-2e0650f0343940eca49601f57dc349ccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of N-(tert-butoxycarbonyl) 4,4-difluoroproline (3.00 g, 11.9 mmol) in THF (20 ml) was added BH3.DMS (1.1 ml, 11.9 mmol) at room temperature. The mixture was heated at reflux for 2 h. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was quenched by the addition of H2O (100 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 75%) as a colorless oil. 1H-NMR (CDCl3) δ1.48 (s, 9 H), 2.04-2.55 (m, 2 H), 3.59-4.17 (m, 5 H). at room temperature The mixture was heated at reflux for 2 h The residue was quenched by the addition of H2O (100 ml) extracted with CHCl3 (2×200 ml) The combined extracts were dried over MgSO4 evaporated The residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) as eluent
Source ID: ord-9f77c9a8aa9348f6bc1a65f05cb78ba1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 8.89 mmol), Et3N (6.2 ml, 44.5 mmol), DMSO (6.3 ml, 88.9 mmol) in CH2Cl2 (20 ml) was added SO3-pyridine (4.25 g, 26.7 mmol). After 3 h stirring, the mixture was concentrated in vacuo and diluted with Et2O (200 ml). The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarbaldehyde (1.40 g, 67%) as a yellow oil. 1H-NMR (CDCl3) δ1.45-1.52 (m, 9 H), 2.49 (m, 2 H), 3.75-3.88 (m, 2 H), 4.29-4.42 (m, 1 H), 9.54 and 9.60 (s, each, total 1 H). the mixture was concentrated in vacuo diluted with Et2O (200 ml) The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml) dried over MgSO4 concentrated in vacuo The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-e5557662dca544ac8e5c4666f7854951Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4difluoro-2-pyrrolidinylmethanol (600 mg, 2.53 mmol), methyl 4-hydroxybenzoate (462 mg, 3.03 mmol), Ph3P (795 mg, 3.03 mmol) in THF (10 ml) was added DIAD (597 ul, 3.03 mmol) at room temperature. The mixture was heated at reflux for 3 h with stirring. After cooling to room temperature, the mixture was concntrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (831 mg, 88%) as a colorless oil. 1H-NMR (CDCl3) δ 1.48 (s, 9 H), 2.53–2.61 (m, 2 H), 3.63–4.41 (series of m, total 8 H), 6.94 (d, J=8.8 Hz, 2H), 7.99(d, J=8.8 Hz, 2H). The mixture was heated at reflux for 3 h The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent
Source ID: ord-b5b8c9b3af584504b4cd88d3d79147c4PubChem References
These sources are listed in the compound's public database record.
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