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

HRID 366308

反応式

HRID 366308 の反応式
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]

参加物

5

反応物 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 679333,3,3-Trifluoropropyl-trimethoxysilaneHCID 178418918HCID 178418918、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
15 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-31698d2f21ca4ea6aba0c55ecb6274f5
出典データセット
uspto-grants-2000_10
特許番号
US06130180

関連ノート

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