Triethylamine → (3-Hydroxy-3-methyl-pyrrolidin-1-yl)-[2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl]-methanone

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Reaction Steps

To a stirred solution of 2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.32 mmol), 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (243 mg, 0.64 mmol) and triethyl amine (0.36 mL, 1.28 mmol) in dichloromethane was added 3-methyl-pyrrolidin-3-ol (66 mg, 0.38 mmol) at room temperature and stirred at room temperature for overnight. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded (3-hydroxy-3-methyl-pyrrolidin-1-yl)-[2-(3-methoxy-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl]-methanone (63 mg, 50%) as a white foam: LC/MS m/e calcd for C24H30N2O3 (M+H)+: 395.52, observed: 395.2.

Provenance & Evidence