Diisopropylamine → Ethyl 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A solution of 7.56 g (74.7 mmol) of diisopropylamine in 100 mL of water-free THF was cooled to −30° C. and n-BuLi (31.9 g, 15% solution in n-hexane, 74.7 mmol mmol) was added via a syringe. The mixture was allowed to stir for 30 min. After cooling to −70° C., 8.68 g (74.7 mmol) tetramethylethylenediamine in 20 mL of THF were added and the mixture was allowed at −70° C. for 1 h. Then, 5 g (34.00 mmol) of 2-methyl-5,6,7,8-tetrahydroquinoline and 3.87 g (35.7 mmol) of ethyl carbonochloridate were added. The mixture was allowed to warm to room temperature within 2 h while being stirring. The reaction mixture was poured onto conc. cold aqueous ammonium chloride solution and extracted with EA (3 times). The combined organic phase was once extracted with a saturated ammonium chloride solution, washed with a saturated sodium bicarbonate solution and dried (magnesium sulfate). After removal of the solvent, the crude product was purified by flash column chromatography (eluent: heptane/EA 1/2) to provide 2.16 g (29%) of the title compound).

Provenance & Evidence