Hydrochloric Acid → HCID 25100943, compound

Participants

Reaction Steps

To a solution of 3-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-indol-1-yl]-propionic acid ethyl ester (25 mg, 0.063 mmol) in ethanol (1 mL) was added 1N aqueous sodium hydroxide solution (1 mL), and the resulting solution stirred for 2 h. The solution was acidified with 1N hydrochloric acid solution before the organic volatiles were removed in vacuo and the aqueous residues were extracted with DCM (3×5 mL). The combined organic phases were dried (MgSO4), filtered, and evaporated in vacuo. The resulting solid was purified by preparative HPLC, dried in vacuo at 50° C. affording 10 mg (43%) of the title compound as a solid. MS-ESI m/z 369; 1H NMR (400 MHz, DMSO) δ 0.81-0.99 (m, 6H), 1.08-1.10 (m, 4H), 1.18-1.22 (m) and 1.50-1.54 (m, 1H), 1.30-1.36 (m, 3H), 1.71-1.73 (m, 1H), 2.24-2.28 (m) and 3.02-3.12 (m, 1H), 2.65 (t, 2H), 3.29 (dd) and 3.68 (dd, 1H), 3.93-3.95 (m) and 4.60-4.62 (m, 1H), 4.29 (t, 2H), 6.24-6.29 (m, 1H), 6.94-6.96 (m, 1H), 7.00-7.12 (m, 2H), 7.27 (d, 1H).

Provenance & Evidence