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1-Adamantanecarboxylic acid → N-(3-hydroxybutyl)adamantane-1-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Adamantanecarboxylic acid | HCID 13235 | — |
| 反応物 | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 2-Butanol, 4-amino- | HCID 170254 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-(3-hydroxybutyl)adamantane-1-carboxamide | HCID 59437164 | 30.2% |
反応手順
Adamantane-1-carboxylic acid (404 mg, 2.24 mmol), 4-amino-butan-2-ol (200 mg, 2.24 mmol), EDCI (885 mg, 4.48 mmol) and HOBt (605 mg, 4.48 mmol) were dissolved in anhydrous CH2Cl2. DIEA (1.444 g, 11.2 mmol) was added to the above mixture at 0° C. under nitrogen. The mixture was stirred overnight and concentrated to give a residue, which was purified by preparative TLC to provide N-(3-hydroxybutyl)adamantane-1-carboxamide (170 mg, 30%). 1H NMR (MeOD, 400 MHz): δ=1.20 (d, 3H), 1.66˜2.04 (m, 17H), 2.87 (m, 2H), 3.79(m, 1H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08835426B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-0bbed32b62c949fca5a7680e4c4e397f |
| 出典メモ | uspto-grants-2014_09 |