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Toluene → 1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Toluene | HCID 1140 | — |
| 反応物 | Diisobutylaluminum hydride | HCID 14487 | — |
| 反応物 | 1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridin-7-one | HCID 67003265 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 1-(1-Naphthalen-1-yl-ethyl)-6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine | HCID 67003261 | 49.8% |
反応手順
To a solution of 4 (4.8 g, 12 mmol) in THF (100 mL) is added slowly 1 M DIBAL in toluene, (50 mL, 50 mmol) at −78° C. The mixture is stirred at room temperature for 1 hour and quenched with 20 mL of water. The solvent is evaporated, the residue is diluted with 100 mL of 1:1 saturated Rochells salt/15% NaOH, and this extracted with EtOAc (4×50 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:9) to provide 2.3 g (48%) of the title compound. M+H+=385.26.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07419975B2 |
| 出典データセット | uspto-grants-2008_09 |
| ORD ID | ord-5948753222ef477090a7d1c6fc09bb4d |
| 出典メモ | uspto-grants-2008_09 |