反应详情

To a solution of tert-Butyl (2R,5R)-2-ethynyl-5-(hydroxymethyl)morpholine-4-carboxylate (0.51 g, 2.1 mmol) in 6 mL of pyridine was added carbonyldiimidazole (0.45 g, 2.8 mmol). The mixture was stirred at ambient temperature for 3 h. Trifluoroethylamine (4.1 mL, 53 mmol) was added, the vessel was sealed and heated to 50° C. for 24 h. The pyridine was removed in vacuo and the residue was dissolved in EtOAc and washed with water and brine. The EtOAc solution was dried (MgSO4), filtered, and the solvent was removed in vacuo. The residue was chromatographed on a 40 g SiO2 column using a gradient elution of 0-50% EtOAc in hexanes. Fractions containing product were combined and removal of solvents in vacuo gave a solid.

1. customthe vessel was sealed
2. temperatureheated to 50° C. for 24 h
3. customThe pyridine was removed in vacuo
4. dissolutionthe residue was dissolved in EtOAc
5. washwashed with water and brine
6. dry with materialThe EtOAc solution was dried (MgSO4)
7. filtrationfiltered
8. customthe solvent was removed in vacuo
9. customThe residue was chromatographed on a 40 g SiO2 column
10. washa gradient elution of 0-50% EtOAc in hexanes
11. additionFractions containing product
12. customremoval of solvents in vacuo
13. customgave a solid