1,2,3,4-Tetrahydroisoquinoline → 3,3,3-Trifluoropropyl(1,2,3,4-tetrahydroisoquinolinyl)dimethoxysilane

HRID 366308

반응식

HRID 366308 반응식
C([Mg]Cl)(C)C.[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.[F:16][C:17]([F:28])([F:27])[CH2:18][CH2:19][Si:20](OC)([O:23][CH3:24])[O:21][CH3:22]>C1COCC1>[F:28][C:17]([F:16])([F:27])[CH2:18][CH2:19][Si:20]([CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1)([O:21][CH3:22])[O:23][CH3:24]

참가 물질

5

반응물 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 679333,3,3-Trifluoropropyl-trimethoxysilaneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 232891393,3,3-Trifluoropropyl(1,2,3,4-tetrahydroisoquinolinyl)dimethoxysilane수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
15 °C

실험 절차

3,3,3-Tritluoropropyl(1,2,3,4-tetrahydroisoquinolinyl)dimethoxysilane--A 500 mL round bottomed flask was charged with tetrahydrofuran (300 mL) and isopropyl-magnesium chloride (30 mL of a 2.0 M solution in THF, 60 mmol). The contents were cooled to 15° C. 1,2,3,4-Tetrahydroisoquinoline (60 mmol) was added over fifteen minutes via pressure equalizing addition funnel. The cold bath was removed and the contents stirred for two hours. 3,3,3-Trifluoropropyltrimethoxysilane (54.5 mmol) was added via pressure equalizing addition funnel. The contents were brought to reflux (65-70° C.) for two hours and reaction progress was monitored by GC. Isolation was accomplished by removing the THF via rotary evaporation, taking the residue up in ether (250 mL), filtration and ether removal via rotary evaporation. Purification was accomplished by distillation to provide 3,3,3-trifluoropropyl(1,2,3,4-tetrahydroisoquinolinyl)dimethoxysilane (54 mmol; 99% yield). C14H20NO2SiF3 (mw=319.39) bp=98° C. at 0.3 mmHg; 1H NMR: (CDCl3) δ 7.2-6.9 (m, 4H), 4.2-4.0 (d, 2H), 3.6-3.4 (s, 6H), 3.3-3.1 (dt, 2H), 2.8-2.6 (m, 2H), 2.2-1.9 (m, 2H), 0.9-0.8 (m, 2H); 13C NMR: (CDCl3) δ 135.9, 135.1, 129.4, 128 (quartet J=275 Hz), 126.0, 125.9, 125.8, 50.4, 46.5, 42.1, 29.9, 28 (quartet, J=30 Hz), 2.8; MS: m/z (relative abundance) 319 (38.3), 318 (100), 222 (7.9), 132 (21.0), 104 (21.4), 79 (9.8), 59 (13.4).

후처리

  1. additionaddition funnel
  2. customThe cold bath was removed
  3. additionaddition funnel
  4. temperatureto reflux (65-70° C.) for two hours
  5. customreaction progress
  6. customby removing the THF
  7. customvia rotary evaporation
  8. filtrationup in ether (250 mL), filtration and ether removal
  9. customvia rotary evaporation
  10. customPurification
  11. distillationwas accomplished by distillation

출처 및 근거

ORD 기록
ord-31698d2f21ca4ea6aba0c55ecb6274f5
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130180

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