Sodium Hydroxide → HCID 69673878, compound

Participants

Reaction Steps

A 50 mL flask containing a solution of tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester (11.1 mg 25.0 μmol) in ethanol (1 mL) and tetrahydrofuran (1 mL) under nitrogen was added sodium hydroxide solution (1.0 M, 250 μL, 250 μmol) and stirred at ambient temperature overnight. Complete conversion was then achieved by heating to 60 C for 30 min. Evaporated in vacuo and azeotroped with toluene (2×5 mL). Residue was taken up in water (10 mL) and acidified to pH=2 with hydrochloric acid solution (2 M) then extracted into ethyl acetate (2×10 mL). Organics were dried with magnesium sulfate and evaporated onto silica gel. Chromatographed using ISCO Companion with a Redisep silica gel 4 g cartridge with an isocratic gradient of ethyl acetate:acetic acid (90:10). Evaporation gave tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid as a colorless solid 7.1 mg (68% Yield). LCMS (12 min acidic) 5.32 min 100% pure by ELSD and UV AP+ and ES+ 418. HNMR (CDCl3) >95% pure 7.77 (br-s, 1H), 7.59 (br-d, 1H), 7.36-7.32 (br-m, 2H), 7.22 (br-d, 1H), 7.10 (br-s, 1H), 5.29 (br-s, 1H), 2.99 (br-t, 2H), 2.85-2.78 (m, 4H), 2.49 (s, 3H), 2.18 (s, 3H), 1.86-1.81 (m, 4H), 0.98 (s, 9H)

Provenance & Evidence