Ethanol → 3-Ethyl-6-hydroxy-7-methoxy-2-(3,4,5-trimethoxybenzyl)tetrahydroisoquinoline

HRID 1944222노트

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HRID 1944222 반응식
C(O)C.[CH2:4]([CH:6]1[CH2:15][CH:14]2[C:9](=[CH:10][C:11]([O:24][CH3:25])=[C:12]([O:16]CC3C=CC=CC=3)[CH2:13]2)[CH2:8][N:7]1[CH2:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=1)[CH3:5]>C1COCC1.[Pd]>[CH2:4]([CH:6]1[CH2:15][CH:14]2[C:9](=[CH:10][C:11]([O:24][CH3:25])=[C:12]([OH:16])[CH2:13]2)[CH2:8][N:7]1[CH2:26][C:27]1[CH:28]=[C:29]([O:37][CH3:38])[C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=1)[CH3:5]

참가 물질

5

반응물 2

HCID 702EthanolHCID 684940673-Ethyl-6-benzyloxy-7-methoxy-2-(3,4,5-trimethoxybenzyl)tetrahydroisoquinoline

생성물 1

HCID 684959363-Ethyl-6-hydroxy-7-methoxy-2-(3,4,5-trimethoxybenzyl)tetrahydroisoquinoline수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Pd/C (10%, 30.7 mg) was covered with THF (2.0 mL) and ethanol (2.0 mL) and stirred under an atmosphere of hydrogen (balloon pressure) for 15 min at room temperature. Then 262 (334 mg, 0.7 mmol) was added as a solution in THF (4.0 mL). The reaction mixture was stirred for 18 h at room temperature, then filtered through celite. The celite was washed with ethyl acetate (4×5 mL) and the combined filtrates were concentrated in vacuo. The residue was recrystallised from ether/dichloromethane to obtain the title compound as yellow solid (253 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 0.98 (3H, t, J 7.4, CH2CH3), 1.41 (1H, sept, J 7.0, one of CH2CH3), 1.68 (1H, sept, J 6.9, one of CH2CH3), 2.51 (1H, dd, J 16.4, 5.9, one of ArCH2CH), 2.75-2.84 (2H, m, one of ArCH2CH, CHN), 3.51-3.75 (4H, m, 2×ArCH2N), 3.80 (3H, s, OCH3), 3.83 (9H, s, 3×OCH3), 6.44 (1H, s, CH), 6.60 (2H, s, 2×CH), 6.65 (1H, s, CH). 13C NMR (100 MHz, CDCl3) δ 11.1, 23.0, 29.4, 50.8, 55.2, 55.9, 56.0, 58.3, 60.9, 105.3, 108.8, 114.6, 125.4, 126.7, 135.6, 136.5, 143.9, 144.9, 153.1. LC/MS (ES+) tr 1.03 min; m/z 388.13 ((M+H)+, 100%); MeOH/H2O 95:5 (1.0 mL/min), HPLC tr 2.58 min (>97%); CH3CN/H2O 90:10 (1.0 mL/min).

후처리

  1. stirringThe reaction mixture was stirred for 18 h at room temperature
  2. filtrationfiltered through celite
  3. washThe celite was washed with ethyl acetate (4×5 mL)
  4. concentrationthe combined filtrates were concentrated in vacuo
  5. customThe residue was recrystallised from ether/dichloromethane

출처 및 근거

ORD 기록
ord-3c59f59ecc0c4016adb12d328188af86
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394825B2

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