Triethylamine → 2-[(r)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine

HRID 1909612노트

반응식

HRID 1909612 반응식
[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28]Cl.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 23392Picolyl chloride hydrochlorideHCID 16222640(2r)-2-[(4-Benzylphenoxy)methyl]pyrrolidine

생성물 1

HCID 160046872-[(r)-2-(4-Benzyl-phenoxymethyl)-pyrrolidin-1-ylmethyl]-pyridine수율 36%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe crude residue was extracted into ethyl acetate (25 mL)
  3. washwashed with water (25 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-c71e8e3b50d44ac1badda7a50a676a41
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598359B2

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