Triethylamine → 7,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid methyl ester

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Reaction Steps

Trifluoro-methanesulfonic acid 7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-2-yl ester (3.1 g, 10.0 mmol) was dissolved in methanol (45 mL) and ethyl acetate (45 mL). PdCl2(dppf)-CH2Cl2 adduct (311 mg, 381 μmol) and triethylamine (1.52 g, 2.1 mL, 15.0 mmol) were added and the mixture was stirred in an autoclave at 110° C. with a CO pressure of 70 bar for 24 h. The solvents were evaporated to give a red-brown oily residue that was purified by gradient chromatography on silica with ethyl acetate in heptane. The chromatography yielded 1.9 g (86%) of the title compound as white solid; LC-MS (UV peak area/EIC) 100%, 220.1335 (M+H)+.

Provenance & Evidence