関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 反応物 | 3-Quinuclidinone | HCID 19507 | — |
| 反応物 | Tosylmethyl isocyanide | HCID 161915 | — |
| 反応物 | Potassium tert-butoxide | HCID 23665647 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 生成物 | 1-Azabicyclo(2.2.2)octane-3-carbonitrile | HCID 142865 | — |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07354930B2 |
|---|
| 出典データセット | uspto-grants-2008_04 |
|---|
| ORD ID | ord-e796ec79918f4833975e03d0b6b9969f |
|---|
| 出典メモ | uspto-grants-2008_04 |
|---|
