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

HRID 1944222ノート

反応式

HRID 1944222 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3c59f59ecc0c4016adb12d328188af86
出典データセット
uspto-grants-2013_03
特許番号
US08394825B2

反応ノート

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