Triethylamine → HCID 10202537, compound

Participants

Reaction Steps

Palladium acetate (224 mg, 1 mmol) was added to a mixture of the carbamate of Example 11 (4.2 g, 10 mmol), triethylamine (2.1 mL, 15 mmol), and t-butyl acrylate (1.76 mL, 12 mmol) in acetonitrile (50 mL) previously degassed with argon for 20 minutes. The resulting mixture was heated at gentle reflux for 26 hours. It was cooled to room temperature. The catalyst was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate, and filtered over a pad of silica gel. Removal of solvent in vacuo afforded the product as an oil (4.0 g, 95%): 1H NMR (CDCl3) δ1.50 (s, 9H), 1.70 1.85 (m, 1H), 200 (m, 1H), 2.80 (m, 2H), 3.40(m, 1H), 3.65 (m, 1H), 5.12 (s, 2H), 5.25 (m, 1H), 6.21 (d, J=15.3 Hz,1H), 6.76 (d, J=8.4 Hz, 1H), 7.20-7.40 (m, 7H), 7.49 (d, J=15.9 Hz, 1H); CI-MS m/z 424 (M+H+).

Provenance & Evidence