反应详情

温度

80 °C

To a solution of (4R*,5R*)-5-[(1S*)(5-bromo(2-thienyl))hydroxymethyl]-1-methyl-4-phenylpyrrolidin-2-one (200 mg, 0.55 mmol) in DMSO (20 mL) was added Et3N (166 mg, 1.64 mmol, 3 equiv), followed by dppf (23 mg, 0.05 mmol, 0.1 equiv), aniline (508 mg, 5.5 mmol, 10 equiv) and palladium(II) acetate (12 mg, 0.05 mmol, 0.1 equiv). The reaction mixture was heated to 80° C. under a CO atmosphere (1 Atm) overnight. The resulting mixture was treated with water (100 mL) and extracted with CH2Cl2 (100 mL). The organic layer was washed with a 1N HCl solution (100 mL) and a saturated NaCl solution (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was triturated (CH2Cl2) to give (±)-5-[(1S*)(5-(N-phenylcarbamoyl)(2-thienyl))hydroxymethyl](4R*,5R*)-1-methyl-4-phenylpyrrolidin-2-one (41 mg, 18%) as a white solid: mp 223-227° C.; TLC (80% EtOAc/hex) Rf 0.26; HPLC ES-MS m/z (rel abundance) 407 (MH+, 100%).

1. extractionextracted with CH2Cl2 (100 mL)
2. washThe organic layer was washed with a 1N HCl solution (100 mL)
3. dry with materiala saturated NaCl solution (100 mL), dried (Na2SO4)
4. concentrationconcentrated under reduced pressure
5. customThe residue was triturated (CH2Cl2)