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Ethyl Acetate → 3-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 2,5-Dibromohexane | HCID 91232 | — |
| 反応物 | tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate | HCID 10401227 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 3-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indol | HCID 19029919 | 30.4% |
反応手順
To a solution of 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole (1.34 g, 4.86 mmol) in acetonitrile (50 mL) were added 2,5-dibromohexane (2.4 g, 9.72 mmol) and potassium carbonate (1.3 g, 9.72 mmol) and the resulting mixture was stirred at reflux for 60 hours. After cooling to room temperature, the solution was poured into ethyl acetate (40 mL), washed with water (40 mL), dried over sodium sulfate and evaporated to dryness. Column chromatography on silica gel using hexane/ethyl acetate (4:1, 2:1 and 1:1) provided the title compound as a syrup (0.65 g, 30%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05654431 |
| 出典データセット | uspto-grants-1997_08 |
| ORD ID | ord-221c90edee9d436da453310cff08c10e |
| 出典メモ | uspto-grants-1997_08 |