Ethanolamine → AGN-PC-009YWY

Participants

Reaction Conditions

Reaction Steps

The adduct 1 (10.0 g, 60.0 mmol) was suspended in methanol (150 mL) and the mixture cooled to 0° C. A solution of ethanolamine (3.6 mL, 60 mmol) in 30 mL of methanol was added dropwise (10 min) to the reaction mixture, and the resulting solution was stirred for 5 min at 0° C., then 30 min at ambient temperature, and finally refluxed for 6 h. After cooling the mixture to ambient temperature, solvent was removed under reduced pressure, and residue was dissolved in 150 mL of CH2Cl2 and washed with 3×100 mL of water. The organic layer was separated, dried over Na2SO4 and filtered. Removal of the solvent under reduced pressure gave white-off solid which was further purified by flash chromatography eluting with ethylacetate (EtOAc) to give the product, 2-(2-hydroxyethyl)-3a,4,7,7a-tetrahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (2), as a white solid. Yield: 3.3 g (27%). 1H NMR (500 MHz, CDCl3, δ): 6.53 (s, 2H, CH═CH, bridge protons), 5.29 (s, 2H, —CHO, bridge-head protons), 3.79-3.70 (m, 4H, NCH2CH2OH), 2.90 (s, 2H, CH—CH, bridge protons). 13C NMR (500 MHz, CDCl3, δ): 176.8, 136.5, 80.9, 60.1, 47.5, 41.7.

Provenance & Evidence