반응 #837113

반응 방정식

solution

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

2-picolyl chloride hydrochloride

triethylamine

→

title compound

수율 36.0%

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

수율 36.0%

용매

DMF

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under reduced pressure
2. 2
   추출The crude residue was extracted into ethyl acetate (25 mL)
3. 3
   세척washed with water (25 mL)
4. 4
   건조The combined organic layers were dried over anhydrous Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude product was purified by flash chromatography

실험 절차

To a solution of Example 1 (0.20 g, 0.66 mmol) in DMF (5 mL) was added 2-picolyl chloride hydrochloride (0.10 g, 0.61 mmol) and triethylamine (0.24 mL, 1.72 mmol). The subsequent mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure. The crude residue was extracted into ethyl acetate (25 mL) and washed with water (25 mL) followed by brine (25 mL). 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 (0.07 g, 36%); 1H NMR (400 MHz, CDCl3); δ 1.73-1.80 (m, 3H), 2.05 (m, 1H), 2.40 (m, 1H), 3.02-3.08 (m, 2H), 3.71 (d, J=13.6 Hz, 1H), 3.83 (m, 1H), 3.91 (s, 2H), 3.95 (m, 1H), 4.25 (d, J=13.6 Hz, 1H), 6.79 (d, J=8.8 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 7.15-7.20 (m, 4H), 7.25-7.27 (m, 2H), 7.41 (m, 1H), 7.61 (m, 1H), 8.53 (m, 1H); MS (m/z) 359.2 (M+1); LC (100.0%).

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