化工社化工社 化学情報印刷レポート · 研究参考用
Acetic Acid → 1h-Indole-1-carboxylic acid,5-[(dimethylamino)methyl]-,1,1-dimethylethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Acetic Acid | HCID 176 | — |
| 反応物 | Dimethylamine | HCID 674 | — |
| 反応物 | Di-tert-butyl dicarbonate | HCID 90495 | — |
| 反応物 | Indole-5-carboxaldehyde | HCID 589040 | — |
| 反応物 | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 1h-Indole-1-carboxylic acid,5-[(dimethylamino)methyl]-,1,1-dimethylethyl ester | HCID 68491935 | 36.2% |
反応手順
In a similar manner to Step 1 of Reference Example 4, 5-formylindole (5.27 g, 36.3 mmol) was dissolved in acetonitrile (100 mL), and the solution was treated with di-tert-butyldicarbonate (9.17 mL, 39.9 mmol) and DMAP (44.0 mg, 0.360 mmol), then the mixture was treated with 51% aqueous dimethylamine solution (72.0 mL, 724 mmol), acetic acid (41.6 mL, 727 mmol) and sodium triacetoxyborohydride (46.2 g, 218 mmol), followed by purification by slurry using diisopropyl ether to obtain 5-(dimethylaminomethyl)-1-(tert-butoxycarbonyl)indole (3.61 g, yield 36%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745641B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-59d0630de42b4180826f17821e743067 |
| 出典メモ | uspto-grants-2010_06 |