関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1,10-Phenanthroline | HCID 1318 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 3-Quinuclidinol, (+)- | HCID 736411 | — |
| 反応物 | 3,7-Dibromo-dibenzothiophene 5,5-dioxide | HCID 4071898 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | HCID 57399776 | HCID 57399776 | 63% |
反応手順
A mixture of 3,7-dibromodibenzothiophene-5,5-dioxide (0.60 g, 1.75 mmol; see J. Med. Chem. 1978, 21, 1084), (S)-(−)-quinuclidin-3-ol (280 mg, 2.2 mmol; Acros), copper(I) iodide (33 mg, 0.17 mmol; Aldrich), 1,10-phenanthroline (63 mg, 0.35 mol; Aldrich) and powdered cesium carbonate (0.86 g, 2.64 mmol; Aldrich) in toluene (2 mL) was heated to 110° C. with vigorous stirring for 30 h. After cooling to room temperature, the reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate and dichloromethane, and the residue purified by flash chromatography (80 g silica gel, 1:10:89 NH4OH-MeOH-CH2Cl2) to afford the title compound (0.37 g, 1.08 mmol; 63% yield): MS (DCl/NH3): m/z 342 (M+1)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07365193B2 |
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| 出典データセット | uspto-grants-2008_04 |
|---|
| ORD ID | ord-17aef5b2e9104056a4f08525966d6bbd |
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| 出典メモ | uspto-grants-2008_04 |
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