Ethyl Acetate → 2-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-N-indan-1-yl-2-phenyl-acetamide

HRID 48571

Reaktionsgleichung

Reaktionsgleichung von HRID 48571
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)CCC1C1(CC(O)=O)C=CC=CC1.C1CN([P+](ON2N=N[C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][C:54]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:69][CH:70]1[C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72][CH2:71]1.[CH:79](N(C(C)C)CC)([CH3:81])[CH3:80].CCO[C:91]([CH3:93])=[O:92]>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:81][CH2:79][CH:80]1[CH:93]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:91]([NH:69][CH:70]1[C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72][CH2:71]1)=[O:92]

Komponenten

8

Edukt 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 123445(+-)-1-AminoindanHCID 2724699PyBOPHCID 697588751-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid

Produkt 1

HCID 227428352-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-N-indan-1-yl-2-phenyl-acetamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid (100 mg, 0.209 mmol) in 5 ml of dry DMF, were added PyBOP (109 mg, 0.209 mmol), 1-aminoindane (32.3 mg, 0.19 mmol) and dropwise diisopropylethylamine (Hünig's base). (75 μl, 0.437 mmol). The mixture reaction was stirred at RT under argon for 20 h. The mixture was then dissolved in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic extracts were dried over MgSO4, filtered and concentrated to give a crude brown residue. Flash chromatography (AcOEt) gave 72 mg (64%) of the title compound as a pale brown oil.

Aufarbeitung

  1. customThe mixture reaction
  2. washwashed with water
  3. extractionThe aqueous phase was extracted twice with CH2Cl2
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude brown residue

Quellen und Nachweise

ORD-Eintrag
ord-527294e8a58b45c3b7dcceae1de8be76
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703392B2

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