暂无可渲染的结构数据
CC(C)(C)OC(=O)N1C[C@H]2CCC(=O)[C@H]2C1中间体产品
tert-butyl (3aR,6aS)-4-oxo-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate
结构、标识符和计算性质已按 CAS 与数据库记录完成匹配。
| 中文名称 | (3AR,6AS)-叔-丁基 4-氧亚基六氢环戊二烯并[C]吡咯-2(1H)-甲酸基酯 |
|---|---|
| English name | tert-butyl (3aR,6aS)-4-oxo-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate |
| IUPAC 名称 | — |
| CAS号 | 1351143-94-6 |
| 数据库编号 | 29948688 |
| 分子式 | — |
| 分子量 | — |
产品信息
(3AR,6AS)-叔-丁基 4-氧亚基六氢环戊二烯并[C]吡咯-2(1H)-甲酸基酯（CAS 1351143-94-6）的产品身份、结构标识及相关反应资料，供化学中间体检索、研发和采购评估使用。
可能的应用方向
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数据库编号 29948688
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合成路线数据
12 条反应 · 12 篇文献
反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 5-Bromo-2-chloropyridine (1.82 g, 9.46 mmol) and the product from Example 44A (1.64 g, 7.28 mmol) were processed as described in Example 1E to afford the title compound (1.25 g, 51%). MS (DCI/NH3) m/z 339, 341 (M+H)+.
来源 ID: ord-80ad559ef03945658b15798c061b31e5反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 5-Bromo-2-chloropyridine (1.82 g, 9.46 mmol) and the product from Example 44A (1.64 g, 7.28 mmol) were processed as described in Example 1E to afford the title compound (1.25 g, 51%). MS (DCI/NH3) m/z 339, 341 (M+H)+.
来源 ID: ord-80ad559ef03945658b15798c061b31e5反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Bromopyridine (4.36 g, 27.6 mmol) and the product from Example 44A (2.07 g, 9.19 mmol) were processed as described in Example 1E to afford the title compound (0.743 g, 27%). MS (DCI/NH3) m/z 305 (M+H)+.
来源 ID: ord-6caac7f76e4848cc80d8020d32b82c90反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Bromopyridine (4.36 g, 27.6 mmol) and the product from Example 44A (2.07 g, 9.19 mmol) were processed as described in Example 1E to afford the title compound (0.743 g, 27%). MS (DCI/NH3) m/z 305 (M+H)+
来源 ID: ord-10ff8feac28343bcaf077713c7794a0e反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Bromopyridine (4.36 g, 27.6 mmol) and the product from Example 44A (2.07 g, 9.19 mmol) were processed as described in Example 1E to afford the title compound (0.743 g, 27%). MS (DCI/NH3) m/z 305 (M+H)+
来源 ID: ord-10ff8feac28343bcaf077713c7794a0e反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: To a solution of (3aR,6aS)-tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (4 g, 17.76 mmol), in tetrahydrofuran (30 mL) at 0° C. was added pyridinium bromide perbromide (6.62 g, 18.64 mmol). The mixture was stirred for 3 hours at room temperature, wherein an ice bath was needed to keep the mixture at about room temperature. The reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL). The mixture was stirred for 0.5 hours and extracted with ethyl acetate. The organic layer was separated and concentrated. The crude product was purified chromatographically using a 40 g silica gel cartridge and eluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes to give (3aR,6aS)-tert-butyl 5-bromo-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate: MS (ESI+) m/z 321 (M+NH4)+. at about room temperature The reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL) The mixture was stirred for 0.5 hours extracted with ethyl acetate The organic layer was separated concentrated The crude product was purified chromatographically eluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes
来源 ID: ord-7961145ce26147bc800b8122478a22bd反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: To a solution of (3aR,6aS)-tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (4 g, 17.76 mmol), in tetrahydrofuran (30 mL) at 0° C. was added pyridinium bromide perbromide (6.62 g, 18.64 mmol). The mixture was stirred for 3 hours at room temperature, wherein an ice bath was needed to keep the mixture at about room temperature. The reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL). The mixture was stirred for 0.5 hours and extracted with ethyl acetate. The organic layer was separated and concentrated. The crude product was purified chromatographically using a 40 g silica gel cartridge and eluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes to give (3aR,6aS)-tert-butyl 5-bromo-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate: MS (ESI+) m/z 321 (M+NH4)+. at about room temperature The reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL) The mixture was stirred for 0.5 hours extracted with ethyl acetate The organic layer was separated concentrated The crude product was purified chromatographically eluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes
来源 ID: ord-7961145ce26147bc800b8122478a22bd反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: Under an inert atmosphere, 1.00 g (4.44 mmol) of tert-butyl (3aR,6aS)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate is dissolved in 15 mL of anhydrous tetrahydrofuran; the medium is cooled to −78° C. and 6.66 mL (6.66 mmol) of a solution of lithium tri-sec-borohydride (L-Selectride) at 1N in tetrahydrofuran are then added dropwise. The medium is allowed to warm to room temperature over three hours with stirring, and then cooled to 0° C., followed by dropwise addition of 35% aqueous hydrogen peroxide solution until the evolution of gas has ceased. The medium is diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. 0.826 g (82%) of the expected product is obtained in the form of a colourless oil. to warm to room temperature over three hours cooled to 0° C. extracted three times with ethyl acetate The combined organic phases are washed once with saturated aqueous sodium chloride solution dried over sodium sulfate filtered concentrated under reduced pressure
来源 ID: ord-b1e86e5597ea46998776f29612adb73c反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: Under an inert atmosphere, 1.00 g (4.44 mmol) of tert-butyl (3aR,6aS)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate is dissolved in 15 mL of anhydrous tetrahydrofuran; the medium is cooled to −78° C. and 6.66 mL (6.66 mmol) of a solution of lithium tri-sec-borohydride (L-Selectride) at 1N in tetrahydrofuran are then added dropwise. The medium is allowed to warm to room temperature over three hours with stirring, and then cooled to 0° C., followed by dropwise addition of 35% aqueous hydrogen peroxide solution until the evolution of gas has ceased. The medium is diluted with water and extracted three times with ethyl acetate. The combined organic phases are washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. 0.826 g (82%) of the expected product is obtained in the form of a colourless oil. to warm to room temperature over three hours cooled to 0° C. extracted three times with ethyl acetate The combined organic phases are washed once with saturated aqueous sodium chloride solution dried over sodium sulfate filtered concentrated under reduced pressure
来源 ID: ord-b1e86e5597ea46998776f29612adb73c反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 5-Bromo-2-chloropyridine (1.82 g, 9.46 mmol) and the product from Example 44A (1.64 g, 7.28 mmol) were processed as described in Example 1E to afford the title compound (1.25 g, 51%). MS (DCI/NH3) m/z 339, 341 (M+H)+.
来源 ID: ord-80ad559ef03945658b15798c061b31e5反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Bromopyridine (4.36 g, 27.6 mmol) and the product from Example 44A (2.07 g, 9.19 mmol) were processed as described in Example 1E to afford the title compound (0.743 g, 27%). MS (DCI/NH3) m/z 305 (M+H)+.
来源 ID: ord-6caac7f76e4848cc80d8020d32b82c90反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: 3-Bromopyridine (4.36 g, 27.6 mmol) and the product from Example 44A (2.07 g, 9.19 mmol) were processed as described in Example 1E to afford the title compound (0.743 g, 27%). MS (DCI/NH3) m/z 305 (M+H)+
来源 ID: ord-10ff8feac28343bcaf077713c7794a0ePubChem References
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