Aluminium lithium hydride → (1-Isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine

Participants

Reaction Conditions

Reaction Steps

6-Amino-1-isopropyl-4,4,7-trimethyl-2-oxo-1,2,3,4-tetrahydroquinoline (12) (0.78 g, 3.2 mmol) was dissolved in tetrahydrofuran (50 mL) and the solution was cooled to 0° C. under argon. The solution was treated with 1M lithium aluminum hydride (4.0 mL, 4.0 mmol) and the reaction stirred at 0° C. to room temperature for 24 hours. The reaction mixture was cooled to 0° C., poured onto ice and extracted with ether (2×). The combined organic extracts were washed with brine and dried (MgSO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (5% ethyl acetate in hexanes) to give the title compound (0.87 g, >100%) as an oil.

Provenance & Evidence