Imidazole → 2-Phthalimidomethyltetrahydroquinoline

HRID 52485

반응식

HRID 52485 반응식
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+].[C:46]1(=[O:56])[NH:50][C:49](=[O:51])[C:48]2=[CH:52][CH:53]=[CH:54][CH:55]=[C:47]12.[K]>O.C1(C)C=CC=CC=1.C(#N)C>[C:46]1(=[O:56])[N:50]([CH2:2][CH:3]2[CH2:12][CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4]2)[C:49](=[O:51])[C:48]2=[CH:52][CH:53]=[CH:54][CH:55]=[C:47]12

참가 물질

9

반응물 6

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 15052240(1,2,3,4-Tetrahydroquinolin-2-yl)methanolHCID 24194345Phthalimide potassium salt

생성물 1

HCID 101083842-Phthalimidomethyltetrahydroquinoline수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 21584213Acetonitrile toluene용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-hydroxymethyltetrahydroquinoline (10 g, 61 mmol), imidazole (10.0 g, 147 mmol), and triphenylphosphine (19.0 g, 72.4 mmol) in a mixed solvent of 5:1 toluene/acetonitrile (360 mL) was added iodine (16.85 g, 66.4 mmol) at 0° C. The mixture was stirred for 2 h at 0° C. and aqueous sodium thiosulfate was added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated. The residue was triturated with diethyl ether and insoluble materials were removed by filtration. The filtrate was concentrated and the residue was dissolved in DMF (60 mL) and potassium phthalimide (13.6 g, 73.48 mmol) was added. The mixture was heated at 60° C. for 2 h and diluted with water (200 mL). The mixture was extracted with 1:1 toluene/ethyl acetate (200 mL×2). The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified with silica gel column chromatography with 10:1 to 6:1 hexane/ethyl acetate to give 10.25 g of 2-Phthalimidomethyltetrahydroquinoline (75%): 1H NMR (270 MHz, CDCl3) δ7.86 (m, 2H), 7.74 (m, 2H), 6.95 (m, 2H), 6.59 (t, 1H, J=8 Hz), 6.49 (d, 1H, J=8 Hz), 3.91 (dd, 1H, J=14, 5 Hz), 3.78 (dd, 1H, J=14, 5 Hz), 3.68 (m, 1H), 2.78 (m, 2H), 2.00 (m, 1H), 1.69 (m, 1H).

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether and insoluble materials
  6. customwere removed by filtration
  7. concentrationThe filtrate was concentrated
  8. dissolutionthe residue was dissolved in DMF (60 mL)
  9. temperatureThe mixture was heated at 60° C. for 2 h
  10. extractionThe mixture was extracted with 1:1 toluene/ethyl acetate (200 mL×2)
  11. washThe organic layers were washed with brine
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated
  14. customThe residue was purified with silica gel column chromatography with 10:1 to 6:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-c19ff97047444c78a2471782a2f7d364
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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