Pyrrolidine → HCID 10570627, compound

Participants

Reaction Steps

Triphosgene (427 mg) is added to a mixture of 3-(4-fluorophenyl)-4,5-dihydroimidazo[1,5-a]quinoxaline (XXXVI, EXAMPLE 247, 702 mg), methylene chloride (27.0 ml) and diisopropylethylamine (0.53 ml) at 0°. The resultant solution is stirred for 1 hr at 0° and for 2 hr at 20°-25°. The mixture is cooled to 0° and pyrrolidine (0.85 ml) is added. The mixture is maintained at 0° for 1 hr and is allowed to warm to 20°-25°. After stirring for 16 basic workup using sodium bicarbonate, methylene chloride and magnesium sulfate and purification by flash chromatography eluting with ethyl acetate/hexane (1/1), pooling the appropriate fractions and concentration gives the product. Recrystallization from hot ethyl acetate-hexane give the title compound, mp 217°-218°; IR (mineral oil) 2925, 1641, 1506, 1414 and 753 cm-1 ; NMR (CDCl3) 8.07, 7.64, 7.53, 7.05-7.3, 4.89, 3.25 and 1.7-1.85 δ; MS (m/z) 362, 264, 98 and 55.

Provenance & Evidence