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 3-quinuclidinone and 41.4 g (212 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. 45.7 g (407 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. After cooling to RT, the resulting solid is filtered off. The filtrate is concentrated and chromatographed on neutral alumina (mobile phase: dichloromethane→ethyl acetate→ethyl acetate/methanol 50:1). 22.9 g (quant.) of the racemic product are obtained in slightly impure form.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US07354930B2 |
|---|
| 출처 데이터셋 | uspto-grants-2008_04 |
|---|
| ORD ID | ord-e796ec79918f4833975e03d0b6b9969f |
|---|
| 출처 메모 | uspto-grants-2008_04 |
|---|
