Hexane → 8-Bromo-6-isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-bromo-6-isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline (Intermediate 5, 6.81 g, 24.9 mmol), and 150 ml of anhydrous THF under argon at −78° C. was slowly added 1.6 M solution of n-butyl lithium and hexane (33 ml, 52.4 mmol). The reaction mixture was stirred at −78° C. for 10 minutes and thereafter N,N-cirmethylformamide (8.0 ml, 100 mmol) was added. The resulting reaction mixture was stirred at −78° C. for 15 minutes and then quenched with saturated NH4Cl. The product was extracted with diethyl ether. The organic layer was washed with water and brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (silica, using 5% ethyl acetate in hexane) to give the title compound as a yellow oil.

Provenance & Evidence