참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 1,2-Dichloroethane | HCID 11 | — |
| 반응물 | Benzhydrol | HCID 7037 | — |
| 반응물 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | Sodium Bicarbonate | HCID 516892 | — |
| 반응물 | 1-Azabicyclo(2.2.2)octane-3-carboxylic acid hydrochloride | HCID 12673436 | — |
| 용매 | Diethyl Ether | HCID 3283 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | Benzhydryl quinuclidine-3-carboxylate | HCID 70926085 | 31.1% |
반응 단계
Quinuclidine-3-carboxylic acid hydrochloride (114 mg, 0.60 mmol), EDC (156 mg, 0.81 mmol), and HOBT (125 mg, 0.81 mmol) were suspended in dry DMF (5 ml). Diphenylmethanol (100 mg, 0.54 mmol) and DIPEA (332 μl, 1.90 mmol) were added, and the mixture was stirred at room temperature for 24 hours. Quinuclidine-3-carboxylic acid hydrochloride (52.0 mg, 0.27 mmol), EDC (52.0 mg, 0.27 mmol), and HOBT (41.6 mg, 0.27 mmol) followed by DIPEA (95 μl, 0.54 mmol) were added again, and the mixture was stirred for 4 days. The reaction was then portioned between sat. NaHCO3 and Et2O. The organic layer was separated, washed again with sat. NaHCO3, water and brine, dried over Na2SO4, filtered, and evaporated to afford benzhydryl quinuclidine-3-carboxylate (54 mg, racemic mixture). The compound was used as such in the next step.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08604015B2 |
|---|
| 출처 데이터셋 | uspto-grants-2013_12 |
|---|
| ORD ID | ord-eff67eb648aa4ff1bc159a4e95e699b4 |
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| 출처 메모 | uspto-grants-2013_12 |
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