反应详情

Methyl 3-cyano-2-phenylpropanoate (350 mg, 1.90 mmol) was treated with LiBH4 (2.28 mmol) in THF (20 ml) at 50° C. for 2 hours until completion of the reaction. It was quenched with water and extracted with ethyl acetate. The organic phase was washed with water, brine and dried with Na2SO4 before being concentrated to dryness. The crude product was then mixed with 3,5-bis(trifluoromethyl)benzyl bromide in DMF (20 ml) and sodium hydride (91 mg, 2.28 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes and quenched with water, and extracted with ethyl acetate. The organic phase was washed with water, brine and concentrated. The crude residue was purified by silica flash chromatography (15% ethyl acetate in hexanes) to afford the desired product (405 mg, 55% in two steps). 1H NMR (500 MHz, CDCl3) δ ppm 2.78 (dd, J=116.79, 7.32 Hz, 1 H) 2.88 (m, 1 H) 3.33 (m, 1 H) 3.81 (m, 2 H) 4.65 (s, 2 H) 7.27 (m, 2 H) 7.31 (m, 1 H) 7.37 (m, 2 H) 7.73 (s, 2 H) 7.80 (s, 1 H).

1. customIt was quenched with water
2. extractionextracted with ethyl acetate
3. washThe organic phase was washed with water, brine
4. dry with materialdried with Na2SO4
5. concentrationbefore being concentrated to dryness
6. additionwas added
7. customquenched with water
8. extractionextracted with ethyl acetate
9. washThe organic phase was washed with water, brine
10. concentrationconcentrated
11. customThe crude residue was purified by silica flash chromatography (15% ethyl acetate in hexanes)