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1,2-Dichloroethane → Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dichloroethane | HCID 11 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | Bis(3-fluorophenyl)methanol | HCID 2758250 | — |
| 反応物 | 1-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride | HCID 12673436 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | Bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate | HCID 70925896 | 57.4% |
反応手順
Quinuclidine-3-carboxylic acid hydrochloride (817 mg, 4.26 mmol), EDC (1.23 g, 6.39 mmol), and HOBT (979 mg, 6.39 mmol) were dissolved in dry DMF (40 ml). DIPEA (2.61 ml, 14.9 mmol) and bis(3-fluorophenyl)methanol (1.03 mg, 4.69 mmol) were added, and the mixture was stirred at room temperature overnight. The mixture was diluted with water and extracted several times with Et2O. The organic phases were collected and washed with brine, dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain bis(3-fluorophenyl)methyl quinuclidine-3-carboxylate (874 mg, racemic mixture).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08604015B2 |
| 出典データセット | uspto-grants-2013_12 |
| ORD ID | ord-e5b17f1598fd4752a8591a206b36f7cb |
| 出典メモ | uspto-grants-2013_12 |