반응 #837115

반응 방정식

solution

(R)-2-(4-Benzylphenoxymethyl)pyrrolidine

triethylamine

methyl 3-bromopropionate

→

title compound

수율 13.3%

3-[(R)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-yl]-propionic acid methyl ester

수율 13.3%

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent was removed under reduced pressure
2. 2
   추출the crude residue was extracted into ethyl acetate
3. 3
   세척The organic portion was washed with water
4. 4
   세척washed with brine
5. 5
   건조dried over anhydrous Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The crude product was purified by silica gel flash chromatography

실험 절차

To a solution of Example 1 (0.2 g, 0.66 mmol) in DMF (5 mL) was added triethylamine (0.16 mL, 1.14 mmol) and methyl 3-bromopropionate (0.07 mL, 0.64 mmol). The resulting slurry was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the crude residue was extracted into ethyl acetate. The organic portion was washed with water, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.03 g, 13%); 1H NMR (400 MHz, CDCl3); δ 1.68-1.80 (m, 3H), 1.93-2.04 (m, 1H), 2.29 (q, J=8.4 Hz, 1H), 2.53 (t, J=7.2 Hz, 2H), 2.70 (m, 1H), 2.87 (m, 1H), 3.13 (m, 1H), 3.24 (m, 1H), 3.66 (s, 3H), 3.75 (m, 1H), 3.92 (s, 2H), 3.93 (m, 1H), 6.82 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.4 Hz, 2H), 7.16-7.20 (m, 3H), 7.27 (m, 2H); MS (m/z) 354.2 (M+1); LC (100.0%).

출처