Water → HCID 67225706, compound

Participants

Reaction Steps

97 mg 8-Dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione (from Step 4) and 45 mg triethylamine are dissolved in 15 ml tetrahydrofuran, and the mixture cooled in an ice bath. Then, 33 mg ethyl chloroformate is added at 0° C. The mixture is allowed to warm to room temperature, and stirred for 2 hours. Then water is added and the mixture extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and the solvent evaporated. The crude product is purified by chromatography on silica gel, with ethyl acetate/methanol/triethylamine (90:5:5) as a solvent, yielding 79 mg Carbonic acid 8-dimethylamino-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester as a solid, mp 162-166° C. 1H-NMR (CDCl3): 7.20 ppm (s, broad, 1H), 6.83 ppm (s, 2H), 4.02 ppm (q, 2H), 3.05 ppm (m, 2H), 2.54 ppm (m, 2H), 2.40 ppm (s, 6H), 2.25 ppm (m, 5H), 2.17 ppm (s, 6H), 1.70 ppm (m, 2H), 1.10 ppm (t, 3H).

Provenance & Evidence