参与物
| 角色 | 名称 | HCID | 投料 |
|---|
| 反应物 | 三乙胺 | HCID 8471 | — |
| 反应物 | 3-氯苯甲醛 | HCID 11477 | — |
| 反应物 | 3-氨基奎宁环盐酸盐 | HCID 197853 | — |
| 反应物 | 三乙酰氧基硼氢化钠 | HCID 5049666 | — |
| 溶剂 | 聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] | HCID 962 | — |
| 溶剂 | 四氢呋喃 | HCID 8028 | — |
| 溶剂 | 二甲基对苯二胺二盐酸 | HCID 14798 | — |
| 产物 | N-[(3-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine | HCID 17158964 | 30% |
反应步骤
A mixture of of 3-aminoquinuclidine dihydrochloride (2.0 g, 10.0 mmol), NEt3 (1.3 mL) and 3-chlorobenzaldehyde (1.5 g, 11.0 mmol) in THF (50 mL) was stirred at room temperature. To this was added Na(OAc)3BH 13.2 g, 15 mmol) and the reaction was stirred overnight. The reaction mixture was diluted with 3N NaOH and water and extracted with EtOAc. The organic extracts were combined, washed with water and then brine and dried over K2CO3. The solution was filtered and the solvent was evaporated in vacuo to give an oil which was chromatographed on silica (94/6 CHCl3/0.5 M NH3 in MeOH). The appropriate fractions were combined and the solvent was evaporated in vacuo to give N-[(3-chlorophenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine (0.75 g, 30%) as an intermediate, a light yellow semi-solid. MH+=251,253. The 1H NMR was consistent with the assigned structure.
来源与证据
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 专利号 | US07179818B2 |
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| 来源数据集 | uspto-grants-2007_02 |
|---|
| ORD ID | ord-91f1822674c442d28b532453a12610e5 |
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| 来源说明 | uspto-grants-2007_02 |
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