Sodium Carbonate → HCID 67618881, compound

Participants

Reaction Steps

To a 50 mL flask containing a stirred suspension of hydroxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester (15.3 mg, 39.0 μmol) in tert-butyl acetate (4 mL) under nitrogen was added perchloric acid (72%, 9.80 uL, 117 μmol) and the clear solution was stirred at ambient temperature for 3 hours. Added sodium carbonate solution (10%) until neutralization had occurred and extracted with ethyl acetate (10 mL). Organics were dried using a hydrophobic frit and evaporated onto silica. Chromatographed using ISCO Companion with a Redisep silica gel 4 g cartridge and a gradient of heptane and ethyl acetate (0-20%). Evaporation gave tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester as a clear oil 11.1 mg (63.8% Yield). LCMS (5 min acidic) 2.66 min 100% pure by ELSD and UV ES+ and AP+ 446. HNMR (CDCl3) >95% pure 7.76 (br-s, 1H), 7.37-7.32 (m, 3H), 7.22-7.20 (m, 1H), 7.03 (br-s, 1H), 5.14 (s, 1H), 4.21-4.15 (m, 2H), 3.00 (br-t, 2H), 2.85-2.73 (m, 5H), 2.50 (s, 3H), 1.88-1.77 (m, 4H), 1.22 (t, 3H), 0.97 (s, 9H).

Provenance & Evidence