関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Boron trifluoride etherate | HCID 8000 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 4-Cyanothiazole | HCID 15069 | — |
| 反応物 | HCID 178418443 | HCID 178418443 | — |
| 触媒 | Titanium isopropoxide | HCID 11026 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | 1-(Thiazol-4-yl)cyclopropanamine | HCID 55285676 | 49.3% |
反応手順
Thiazole-4-carbonitrile (1035 mg, 9397 μmol) was azeotroped with toluene. Et2O was added, and the clear solution was cooled to −70° C., followed by addition of titanium tetraisopropoxide (3025 μl, 10337 μmol), and ethylmagnesium bromide (6265 μl, 18795 μmol). The reaction mixture turned yellow. It remained yellow until about 15 min. The reaction was raised to RT, the solution changed into black. After 1 h., boron trifluoride diethyl etherate (2361 μl, 18795 μmol) was added and stirred for 1.5 hr. Then 1N HCl 27 mL was added, followed by 100 mL ether, 95 mL 10% NaOH. The reaction was extracted with Et2O×2 and 30% IPA/CHCl3×1. The organic layer was concentrated and purified with silica gel chromatography using 0-10% MeOH/DCM. 650 mg of product 14.2.B was obtained in 49% yield.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08785468B2 |
|---|
| 出典データセット | uspto-grants-2014_07 |
|---|
| ORD ID | ord-ae043e8723ad458a9b60ddee57e3eb51 |
|---|
| 出典メモ | uspto-grants-2014_07 |
|---|
