Ethyl Acetate → Methyl 2-(3-(benzyloxycarbonyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-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-6-carboxylate (14.0 g, 31.4 mmol, 1.0 eq.), triethylsilane (10.6 g, 91.4 mmol, 2.91 eq.) in dichloromethane (240 mL), which was placed in a drop funnel, under nitrogen below 0° C. over 1 h. colorless solution turned yellow gradually. The resulting mixture was allowed to warm back to room temperature naturally overnight. Thin layer chromatography (Petroleum ether:ethyl acetate=3:1) showed the reaction was complete. The reaction mixture was basified with solid sodium carbonate to pH=7 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (Petroleum ether:ethyl acetate=10:1) to give 10.2 g of methyl 2-(3-(benzyloxycarbonyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a yellow oil, yield: 75.6%. MS (ESI+APCI) M+1=430.2.

Provenance & Evidence