Dicyclohexylcarbodiimide → 1,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinoline

HRID 1088695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088695
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.O.OC1C2N=NNC=2C=CC=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][CH2:30][C:31](O)=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:31](=[O:32])[CH2:30][CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:6]2

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 7031693-(2-Thienyl)propanoic acidHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 157186901,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinolineAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,2,3,4-tetrahydro-6-methoxyisoquinoline (3.29 g), hydroxybenzotriazole monohydrate (5.72 g) and 3-(2-thienyl)propanoic acid (3.31 g) in 280 ml of dry tetrahydrofuran (THF) at 0° C. was added DCC (4.37 g) in one portion. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was filtered and concentrated. The residue was taken up into 200 ml of ethyl acetate (EtOAc) refiltered, washed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml), dried (MgSO4), filtered, and concentrated. Chromatography on silica gel (elution with 20% EtOAc:hexanes) afforded 4.54 g of the desired product.

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. washwashed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e5072f731db4fcb96a87b0bdc848440
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963563

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