참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Boron trifluoride etherate | HCID 8000 | — |
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | 4-Cyanothiazole | HCID 15069 | — |
| 반응물 | HCID 178418443 | HCID 178418443 | — |
| 촉매 | Titanium isopropoxide | HCID 11026 | — |
| 용매 | Toluene | HCID 1140 | — |
| 용매 | Diethyl Ether | HCID 3283 | — |
| 생성물 | 1-(Thiazol-4-yl)cyclopropanamine | HCID 55285676 | 49.3% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08785468B2 |
|---|
| 출처 데이터셋 | uspto-grants-2014_07 |
|---|
| ORD ID | ord-ae043e8723ad458a9b60ddee57e3eb51 |
|---|
| 출처 메모 | uspto-grants-2014_07 |
|---|
