반응 #837142

반응 방정식

potassium carbonate

(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine

DMF

methyl 3-bromopropionate

→

title product

수율 14.0%

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

수율 14.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITleft
3. 3
   기타to react overnight
4. 4
   추출extracted with ethyl acetate (3×)
5. 5
   세척The combined ethyl acetate layers were washed with brine
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   농축concentrated to dryness
8. 8
   기타The compound was then purified by flash chromatography (
9. 9
   세척eluted with 1% methanol in dichloromethane with a 30:1 silica ratio)

실험 절차

(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine (200 mg, 0.658 mmol) was taken into DMF (2 mL), and methyl 3-bromopropionate (121 mg, 0.724 mmol) was added, followed by potassium carbonate (182 mg, 1.317 mmol). The mixture was heated to 60° C. and left to react overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The compound was then purified by flash chromatography (eluted with 1% methanol in dichloromethane with a 30:1 silica ratio) to obtain the title product (32.6 mg, 0.092 mmol, 14% yield); LCMS; m/z 353.47. found 354.3 (M+1). 1H NMR (400 MHz, CDCL3) δ 3.92 (s, 1H), 1.59 (s, 2H), 1.76-1.78 (m, 1H), 1.93-2.00 (m, 1H), 2.28-2.30 (m, 1H), 2.52-2.55 (m, 2H), 2.67-2.74 (m, 1H), 2.84-2.91 (m, 1H), 3.11-3.15 (m, 1H), 3.20-3.27 (m, 1H), 3.66 (s, 3H), 3.73-3.77 (m, 1H), 3.91-3.92 (m, 2H), 6.81-6.84 (m, 2H), 7.07-7.09 (m, 2H), 7.16-7.29 (m, 5H).

출처