Hexane → HCID 11499733, compound

Participants

Reaction Steps

To a solution of 1′-ethyl-6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline] (100 mg) in 2 mL chloroform cooled in ice bath (10° C.) was added BBr3 (2 mL, 1 M). After 4 hours, ice was added to quench the reaction. After separation of the two layers, dichloromethane was used to extract the aqueous phase. The combined organic phases were then washed with brine, dried and evaporated to give a crude oil which was then passed through a column (EtOAc: Hexane; 2-16%) to give 1′-ethyl-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-6′-ol (35.9 mg). 1H-NMR (300 MHz, CDCl3): δ=6.37 (s, 1H), 3.04 (s, 2H), 2.95-2.65 (q, 2H), 2.74 (s, 2H), 2.12 (s, 3H), 2.1 (s, 3H), 2.05-1.85 (m, 4H), 1.84-1.64 (m, 2H), 1.3-1.1 (t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=152.88, 143.52, 133.97, 130.4, 126.13, 116.74, 62.54, 55.07, 44.81, 42.13, 36.29, 19.77, 19.31, 16.6, and 15.79 ppm. MS: (m/z): 246.2 (M+H+)

Provenance & Evidence