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methyl 2-(1-(3-methylbutanoyl)-1,2,3,4-tetrahydroquinolin-6-yl)acetate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 2.0h;Inert atmosphere;
To a stirred solution of methyl 2-(l,2,3,4-tetrahydroquinolin-6-yl)acetate (673 mg, 2.95 mmol) in DCM (10 mL) were added Et3N (1.4 mL, 10.10 mmol) and 3-methylbutanoyl chloride (534 mg, 4.43 mmol) dropwise at 0 C under nitrogen atmosphere. After the addition was finished the reaction was stirred at 20 C for 2 h and LCMS showed the reaction was complete. The mixture was quenched with MeOH (2 mL), then the solvent was removed in vacuo. The residue was re-dissolved in DCM (50 mL) and diluted with water (100 mL), extracted with DCM (30 mL chi 2), the combined organic layers were washed with brine (30 mL), dried over Na2SC>4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (S1O2) (eluting with Petroleum ether/ethyl acetate =15: 1 to 5: 1) to give methyl 2-(l-(3-methylbutanoyl)-l,2,3,4-tetrahydroquinolin-6-yl)acetate as an oil. LCMS m/z (M+H+) calc'd 290.1, found 290.0
tert-butyl 6-(2-methoxy-2-oxoethyl)-3,4-dihydroquinoline-1-(2H)-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In acetonitrile; at 20℃; for 24.0h;
To a solution of methyl 2-(l,2,3,4-tetrahydroquinolin-6-yl)acetate (2000 mg, 9.74 mmol) in ACN (10 ml) was added BOC-anhydride (2.71 ml, 11.69 mmol) at RT. The reaction was monitored by TLC and the starting material was found converted after 24 h as shown by LCMS. The solvent was removed under vacuum and the residue was purified using Combi- Flash, eluting with Hexane/ethyl acetate: ethanol (3: 1) with starting hexane=100% and end Hexane = 20%. The desired product was obtained as an oil. LCMS m/z (M+H) calc'd: 306.1 ; found: 306.1.
With palladium 10% on activated carbon; hydrogen; In ethanol; at 50℃; under 1551.49 Torr; for 12h;
To a solution of methyl 2-(quinolin-6-yl)acetate (700 mg, 3.30 mmol) in ethanol (20 mL) was added Pd/C (400 mg, 0.376 mmol)(10percent), and the reaction was stirred at 50 °C under 30 psi of hydrogen. The reaction was monitored by LCMS. After stirring for 12 h the reaction was finished. The catalyst was removed off by filtration, and the filtrate was concentrated in vacuo to give the title compound as an oil. LCMS m/z (M+H+) calc'd 206.1, found 206.0
To a suspension of 2-(1,2,3, 4-tetrahydroquinolin-6-yl)acetic acid (1 g, 5.23 mmol) in DCM (5 ml) at 0 C was added trimethylsilyldiazomethane in hexane (7.84 ml, 15.69 mmol) dropwise. Gas was evolved from the reaction mixture during the addition. After the completion of addition, the mixture was concentrated and purified using flash column chromatography (eluting with hexane/ethyl acetate: ethanol = 3: 1, starting with 100% hexane, end with 20% hexane) to give the desired product as an oil. LCMS m/z (M+H) calc'd: 206.1 ; found: 206.1.
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