Boron trifluoride etherate → 2-[1-(3,4-dimethoxy-benzyl)-7-(1-methyl-prop-2-oxy)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

HRID 48850

Reaktionsgleichung

Reaktionsgleichung von HRID 48850
ClC(Cl)(Cl)C(=N)O[C:5]([CH3:8])([CH3:7])C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([OH:28])[CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:31][C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].B(F)(F)F.[CH3:51]COCC.C([O-])(O)=O.[Na+]>ClCCl.C1CCCCC1.C(OCC)(=O)C.O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([O:28][CH:5]([CH3:7])[CH2:8][CH3:51])[CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:31][C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]

Komponenten

9

Edukt 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate2×HCID 227427542-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

Produkt 1

HCID 227427802-[1-(3,4-dimethoxy-benzyl)-7-(1-methyl-prop-2-oxy)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamideAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8078CyclohexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

At room temperature tert.-butyl 2,2,2-trichloroacetimidate (437 mg, 0.36 mL, 2.0 mmol) was added to a solution of 2-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide (95.3 mg, 0.2 mmol) in dichloromethane (5.0 mL) and cyclohexane (5.0 mL). The reaction mixture was treated with a solution of boron trifluoride diethyl etherate (50 μL, 0.4 mmol) in 10 mL dichloromethane and stirred for 22 h. Another portion of tert.-butyl 2,2,2-trichloroacetimidate (244 mg, 0.20 mL, 1.1 mmol) was added. After stirring for three days a saturated solution of NaHCO3 (10 mL), water (10 mL) and ethyl acetate (40 mL) were added, the phases were separated and the aqueous phase was extracted three times with ethyl acetate (30 mL). The combined organic phases were concentrated in vacuo and purified by flash-chromatography to give the titled product (80.4 mg, 75%) as pale yellow oil.

Aufarbeitung

  1. additionwere added
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with ethyl acetate (30 mL)
  4. concentrationThe combined organic phases were concentrated in vacuo
  5. custompurified by flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-940fa4589911448486d2b30bb65761f7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703392B2

Verknüpfte Notizen

Wird geladen…