Réaction #330397

Équation de réaction

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

Rendement 49.0%

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

Rendement 49.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was cooled in an ice bath
2. 2
   Lavagewashed with aqueous Na2CO3
3. 3
   SéchageThe organic layer was dried (Na2SO4)
4. 4
   Concentrationconcentrated in vacuo
5. 5
   AutreThe resulting residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane)

Mode opératoire

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

Source