반응 #1996795

반응 방정식

solution

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

4-picolyl chloride hydrochloride

triethylamine

→

title compound

수율 45.0%

4-[(R)-2-(4-benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine

수율 45.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   추출The crude product was extracted into dichloromethane
2. 2
   세척washed with water
3. 3
   건조The combined organic layers were dried over anhydrous Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude product was purified by flash chromatography

실험 절차

To a solution of Example 1 (0.25 g, 0.82 mmol) in dichloromethane (2 mL) was added 4-picolyl chloride hydrochloride (0.13 g, 0.79 mmol) and triethylamine (0.29 mL, 2.08 mmol). The resulting mixture was stirred at ambient temperature overnight. The crude product was extracted into dichloromethane and washed with water followed by brine. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.11 g, 45%); 1H NMR (400 MHz, CDCl3); δ 1.70-1.81 (m, 3H), 2.03 (m, 1H), 2.27 (m, 1H), 2.94-3.03 (m, 2H), 3.49 (d, J=14.4 Hz, 1H), 3.86 (m, 1H), 3.92 (s, 2H), 3.94 (m, 1H), 4.19 (d, J=14.4 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 3H), 7.26-7.29 (m, 4H), 8.51 (m, 2H); MS (m/z) 359.5 (M+1); LC (99.7%); HPLC (91.6%)

출처