반응 #837144

반응 방정식

potassium carbonate

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

DMF

t-butylbromoacetate

→

title product

수율 64.3%

[(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-yl]-acetic acid tert-butyl ester

수율 64.3%

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 sodium sulfate
7. 7
   농축concentrated to dryness
8. 8
   기타The compound was then purified by flash chromatography (
9. 9
   세척eluted with 0.5% methanol in dichloromethane with a 40:1 silica ratio)

실험 절차

(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine (200 mg, 0.658 mmol) was taken into DMF (2 mL), and t-butylbromoacetate (141 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 sodium sulfate, and concentrated to dryness. The compound was then purified by flash chromatography (eluted with 0.5% methanol in dichloromethane with a 40:1 silica ratio) to obtain the title product (161 mg, 0.423 mmol, 64% yield); LCMS; m/z 381.52. found 381 (M). 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 1.66-1.73 (m, 2H), 1.79-1.85 (m, 2H), 1.99-2.06 (m, 1H), 2.63-2.69 (m, 1H), 3.18-3.22 (m, 2H), 3.40 (d, J=17.2, 1H), 3.59 (d, J=16.8, 1H), 3.79-3.83 (m, 1H), 3.91-3.95 (m, 2H), 6.82 (d, J=8.88, 2H), 7.08 (d, J=8.8, 2H), 7.15-7.27 (m, 5H).

출처