Diisopropylethylamine → HCID 9949180, compound

Participants

Reaction Steps

To a stirred solution of (R)-1-Aza-bicyclo[2.2.2]oct-3-ylamine dihydrochloride (25 g, 0.125 mol), 3-(phenylthio)acrylic acid (23.5 g, 0.13 mol), and diisopropylethylamine (90 ml) in dry DMF (600 ml) at ambient temperature was added in succession 1-hydroxybenzotriazole hydrate (17 g, 0.126 mol) and O-benzotriazol-1-yl-N.N,N′,N′-tetramethyluronium tetrafluoroborate (40 g, 0.124 mol). The resulting amber-colored solution was stirred overnight, diluted with water (1 vol), and extracted with ether (2×700 ml). The aqueous phase was made basic (pH 10) with 50% aqueous sodium hydroxide and extracted with chloroform (3×700 ml). The chloroform extracts were combined, washed with water, brine, dried over sodium sulfate and concentrated to dryness to give crude product as a syrup (40 g). The syrup was taken in isopropanol (IL), made acidic with gaseous HCL, and allowed to stand. The resulting solid was collected by filtration, recrystallized from isopropanol (2×), and dried in vacuo to give the title compound (8 g) as a white solid. MS (ES+) 289. (MH30).

Provenance & Evidence