関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 4-Phenylpiperidine-4-methanol | HCID 77896 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | Trifluoromethanesulfonic acid 1-butyl-3-chloro-2-oxo-1,2-dihydropyridin-4-yl ester | HCID 25221428 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | (Trifluoromethyl)benzene | HCID 7368 | — |
| 生成物 | 1'-Butyl-3'-chloro-4-hydroxymethyl-4-phenyl-3,4,5,6-tetrahydro-2H,1'H-[1,4]bipyridinyl-2'-one | HCID 59497081 | — |
反応手順
4-Hydroxymethyl-4-phenylpiperidine (0.172 g, 0.9 mmol), palladium(II) acetate (0.007 g, 0.03 mmol), cesium carbonate (0.391 g, 1.2 mmol) and Xantphos (0.035 g, 0.06 mmol) were added to a solution of intermediate D9 (0.2 g, 0.6 mmol) in trifluoromethylbenzene (2 ml). The reaction mixture was heated at 100° C. for 24 hours in a sealed tube, after which it was cooled to room temperature. Subsequently, it was diluted with DCM, H2O (5 ml) and extracted with EtOAc (3×5 ml). The mixture was filtered through diatomaceous earth, and the filtrate was evaporated to dryness. The crude product was purified first by column chromatography (silica gel; eluent: DCM/EtOAc from 90/10 to 0/100) and then by reversed phase HPLC. The desired fractions were collected, evaporated in vacuo and finally freeze dried to yield compound E22 (0.041 g, 18%) as a white foam.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09114138B2 |
|---|
| 出典データセット | uspto-grants-2015_08 |
|---|
| ORD ID | ord-b68423f2e2fb4211b3f631f86f3b2c52 |
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| 出典メモ | uspto-grants-2015_08 |
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