Trifluoroacetic acid → Methyl 2-(3-(benzyloxycarbonyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate

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Reaction Steps

To a solution of methyl 2-(3-(benzyloxycarbonyl)phenyl)-4-hydroxy-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate (0.66 g, 1.49 mmol), triethylsilane (0.5 g, 4.3 mmol) in dichloro methane (10 mL) was added a solution of trifluoroacetic acid (0.69 g, 6.1 mmol), which was placed in a drop funnel, under nitrogen with ice cooling. Upon completion of addition, the resulting mixture was allowed to warm back to room temperature naturally overnight. Thin layer chromatography (petroleum ether:ethyl acetate=20:1) showed the reaction was complete. The reaction mixture was basified with solid sodium carbonate to pH=6 and filtered. The filtrate was concentrated in vacuo and the residual was purified by column chromatography (petroleum ether:ethyl acetate=25:1) to give 109 mg of methyl 2-(3-(benzyloxycarbonyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-8-carboxylate as a off-yellow solid, yield: 39.6%.

Provenance & Evidence