反应详情

To a solution of BOP (234 mg, 0.529 mmol), TEA (0.074 mL, 0.529 mmol) and DMAP (129 mg, 1.058 mmol) in dichloromethane (10 mL) and DMF (10 mL) was added 2E in dichloromethane (10 mL) via a syringe pump over 10.0 h. The reaction was continued at rt for 4 h, quenched by water and extracted by EtOAc (×3). The combined organics were washed by brine, dried with Na2SO4 and concentrated. The crude product was purified by flash chromatography (loading in chloroform, 0% to 100% ethyl acetate in hexane over 10 min using a 4 g silica gel cartridge) to give a mixture of diastereoisomers (92 mg, 43% yield). The diastereoisomers were separated to give 2F (30 mg, 0.037 mmol, 32.6% yield) using a R,R-Welko-O 1 column (21.1 mm×250 mm, 10 micron, Regis Technologies, Inc.). MS (ESI) m/z: 814.7 (M+H)+.

1. customquenched by water
2. extractionextracted by EtOAc (×3)
3. washThe combined organics were washed by brine
4. dry with materialdried with Na2SO4
5. concentrationconcentrated
6. customThe crude product was purified by flash chromatography (loading in chloroform
7. wait0% to 100% ethyl acetate in hexane over 10 min using
8. customa 4 g silica gel cartridge) to give
9. additiona mixture of diastereoisomers (92 mg, 43% yield)
10. customThe diastereoisomers were separated