Ethylene carbonate → HCID 22873792, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(2-ethylsulphonylethyl)-3-(2(R)-pyrrolidinylmethyl)-1H-indole (Preparation 5; 350 mg, 1.1 mmol) in dry dimethylformamide (10 ml) at room temperature under nitrogen was added ethylene carbonate (160 mg, 1.8 mmol). The mixture was heated at 120° C. for 18 hours, allowed to cool, then partitioned between ethyl acetate and water. The organic phase was separated, washed with water (3×), dried (Na2SO4) and evaporated under reduced pressure to give a foam. Purification by column chromatography on silica gel, eluting initially with dichloromethane followed by a gradient of 0.880 aqueous ammonia:ethanol: dichloromethane (0:10:90 to 0.5:10:90), afforded the title compound as gum. Rf 0.35 (SS 4). Found: C,62.29; H,7.73; N,7.23. C19H28N2O3S; 0.05 CH2Cl2 requires C,62.04; H,7.68; N,7.60%. δ(CDCl3): 1.35(3H,t), 1.50-1.90(5H,m), 2.30(1H,m), 2.50(1H,m), 2.70(1H,m), 2.80-3.35(10H,m), 3.60-3.75(2H,m), 5.30(0.10H,s,CH2Cl2), 7.00(1H,d), 7.05(1H,s), 7.25(1H,d), 7.40(1H,s), 8.25(1H,br s).

Provenance & Evidence