Ethanolamine → AGN-PC-009YWY

Temperature

0 °C

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.

1. temperature30 min at ambient temperature, and finally refluxed for 6 h
2. temperatureAfter cooling the mixture to ambient temperature
3. customsolvent was removed under reduced pressure, and residue
4. dissolutionwas dissolved in 150 mL of CH2Cl2
5. washwashed with 3×100 mL of water
6. customThe organic layer was separated
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customRemoval of the solvent under reduced pressure
10. customgave white-off solid which
11. customwas further purified by flash chromatography
12. washeluting with ethylacetate (EtOAc)

ORD record

ord-637919f0ff9f46648b663b8488db4d70

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09415123B2