反应详情

To a solution of 2-allyl phenyl acetic acid (0.050 mg, 0.284 mmol) in Dimethylformamide (5 mL) was added 3-[3-(Dimethylamino)propyl]-1-ethylcarbodiimide hydrochloride (EDCI, 0.075 mmol, 0.397 mmol), 1-Hydroxy-7-azabenzotriazole (HOAt, 0.054 mg, 0.397 mmol), (2R,5R)-dimethylpyrrolidine (0.034 mL, 0.298 mmol) followed by triethylamine (0.118 mL, 0.851 mmol). The solution was stirred for 18 h and water was added (20 mL). The aqueous layer was extracted with diethylether and the combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (9/1 the 4/1) to give 2-(2-allyl-phenyl)-1-((2R,5R)-2,5-dimethyl-pyrrolidin-1-yl)-ethanone (colourless oil, 73 mg, 99%). C17H23NO; MW: 257.38; LCMS (method A) RT 1.84 min; ES 258 (100%, MH+), 280 (10%, MNa+); 1H NMR (400 MHz, CDCl3) δ 7.08-7.24 (4H, m), 5.97 (1H, m), 5.07 (1H, m), 4.99 (1H, m), 4.29 (1H, q), 4.01 (1H, q), 3.76 (1H, d), 3.58 (1H, d), 3.39 (2H, m), 2.08-2.26 (2H, m), 1.52-1.63 (2H, m), 1.23 (3H, d), 1.21 (3H, d) ppm.

1. extractionThe aqueous layer was extracted with diethylether
2. washthe combined organic layers were washed with brine
3. customdried
4. concentrationconcentrated
5. customThe residue was purified by flash chromatography
6. washeluting with cyclohexane and ethyl acetate (9/1 the 4/1)