Ammonium Chloride → HCID 178498378, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 100 mg of 2-(1-Amino-ethylidene)-malonic acid dimethyl ester (57.7 μmol) and 168 mg of 2,2-dimethyl-1-methylpyrrolidine (115.4 μmol) in 2 mL of toluene was heated at reflux for 3 h then 160 mg of sodium tert butoxide (2.9 eq) and 1 mL of tert butanol was added. The resulting reaction mixture was heated at 90° C. and stirred for 16 h then cooled to room temperature. To this solution was added 5 mL of aqueous saturated ammonium chloride and was extracted with three portions of 10 mL of ethyl acetate. The combined organic layer was washed with brine and dried (MgSO4). After the solvent was removed under diminished pressure, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:20 to 1:10 EtOAc-hexanes gave product 28 as white solid: yield 115 mg, (90%); Silica gel TLC Rf 0.46 (1:4 EtOAc-Hexane); 1H NMR (CDCl3, ppm): δ 2.62 (s, 3H), 2.93 (t, J=8.4 Hz, 2H), 2.98 (s, 3H), 3.55 (t, J=9.0 Hz, 2H), 3.90 (s, 3H), 11.79 (s, 1H). 13C NMR (CDCl3, ppm): δ 22.48, 27.82, 31.90, 51.98, 52.35, 101.09, 102.20, 162.20, 163.75, 165.64, 172.38; HRMS (ESI+) calculated for C11H14N2O3 223.1077. found 223.1082.

Provenance & Evidence