참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 반응물 | 3-Quinuclidinone | HCID 19507 | — |
| 반응물 | Tosylmethyl isocyanide | HCID 161915 | — |
| 반응물 | Potassium tert-butoxide | HCID 23665647 | — |
| 용매 | Ethanol | HCID 702 | — |
| 생성물 | 1-Azabicyclo(2.2.2)octane-3-carbonitrile | HCID 142865 | — |
반응 단계
20.4 g (163 mmol) of quinuclidin-3-one and 41.37 g (211.87 mmol) of (4-toluenesulfonyl)methyl isocyanide are introduced into 435 ml of 1,2-dimethoxyethane and 16 ml of dry ethanol while cooling in ice. 45.72 g (407.45 mmol) of potassium tert-butoxide are slowly added in such a way that the temperature does not rise above 10° C. The mixture is then heated at 40° C. for 2.5 h. The solid resulting at RT is filtered off. The filtrate is concentrated and chromatographed on neutral alumina (mobile phase: initially dichloromethane, then ethyl acetate→ethyl acetate/methanol 50:1). 22.9 g (103% of theory) of the product are obtained in slightly impure form.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US07138410B2 |
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| 출처 데이터셋 | uspto-grants-2006_11 |
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| ORD ID | ord-daecf57368fc403498d8147dbfcfd830 |
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| 출처 메모 | uspto-grants-2006_11 |
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