Potassium Carbonate → 2-(dimethylamino)ethyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

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Reaction Steps

To a solution of lithium 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 20) (246 mg, 0.591 mmol) and 2-bromo-N,N-dimethylethanamine (135 mg, 0.886 mmol) in DMF (5 mL) was added potassium carbonate (122 mg, 0.886 mmol). The resulting mixture was stirred at room temperature for 2 h, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in a 1:1 MeOH/DMSO mixture and purified by MDAP (formate). The appropriate fractions were combined and concentrated in vacuo to give 2-(dimethylamino)ethyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (14.5 mg, 5%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.72 min, MH+=482.

Provenance & Evidence