Triethylamine → 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl ester

HRID 48569

Reaktionsgleichung

Reaktionsgleichung von HRID 48569
Cl.[CH3:2][O:3][C:4]1[C:24]([O:25][CH3:26])=[CH:23][C:7]([CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11]N2)=[CH:6][CH:5]=1.[CH2:27](N(CC)CC)C.[CH3:34][O:35][C:36](=[O:45])[CH:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:34][O:35][C:36](=[O:45])[CH2:37][C:38]1([CH:27]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:9]2[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[C:24]([O:25][CH3:26])[CH:23]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 16667431Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1)HCID 21226206Ethyl acetate hexane

Produkt 1

HCID 697601251-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl esterAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a white suspension of 1-(4,5-dimethoxybenzyl)6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (5 g, 0.013 mol) in dry toluene (50 ml), were added triethylamine (5.5 ml, 0.039 mol) and bromo-phenyl-acetic acid methyl ester (2.07 ml, 0.013 mol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt/hexane 1/1) gave 5.85 g (90%) of the title product as a brown-orange oil.

Aufarbeitung

  1. temperatureat reflux under argon for 20 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude brown-orange oil

Quellen und Nachweise

ORD-Eintrag
ord-ea68a220f4284ba196011734ad7e3a3e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703392B2

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