反应 #330397

反应方程式

5-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylamine

5-fluoro-2-methylquinolin-8-ylamine

(S)-2-tert-butoxycarbonylaminopropionic acid

HOAt

EDCI HCl

→

title compound

收率 49.0%

[(S)-1-(5-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

收率 49.0%

溶剂

DCM

DCM

反应条件

后处理

1. 1
   温度The mixture was cooled in an ice bath
2. 2
   洗涤washed with aqueous Na2CO3
3. 3
   干燥The organic layer was dried (Na2SO4)
4. 4
   浓缩concentrated in vacuo
5. 5
   其他The resulting residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane)

实验过程

To the mixture of 5-fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-ylamine and 5-fluoro-2-methylquinolin-8-ylamine from the previous step (0.369 mmol) in DCM (10 mL) was added (S)-2-tert-butoxycarbonylaminopropionic acid (76.8 mg, 0.405 mmol) and HOAt (56 mg, 0.41 mmol). The mixture was cooled in an ice bath, then EDCI HCl (85 mg, 0.44 mmol) was added. The reaction mixture was stirred in the ice bath for 2 h, then diluted with DCM, washed with aqueous Na2CO3 and then water. The organic layer was dried (Na2SO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane) affording the title compound as a colourless solid (63.6 mg, 49%, 2 steps). LCMS (Method J): RT 3.40 min [M+H]+ 352

来源