Sodium Iodide → [4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl ester

HRID 1988118

Reaktionsgleichung

Reaktionsgleichung von HRID 1988118
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:16]3[CH:9]([CH2:10][C:11](=[O:17])[C:12]=3[C:13]=1[O:14][CH3:15])[NH:8][CH2:7][CH2:6]2.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36]Br)([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C.C(OCC)(=O)C.O>[C:26]([O:30][C:31](=[O:38])[NH:32][CH2:33][CH2:34][CH2:35][CH2:36][N:8]1[CH2:7][CH2:6][C:5]2[C:16]3[CH:9]1[CH2:10][C:11](=[O:17])[C:12]=3[C:13]([O:14][CH3:15])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH3:29])([CH3:28])[CH3:27]

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 577290647,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one

Produkt 1

HCID 57729072[4-(7,8-Dimethoxy-1-oxo-2,2a,4,5-tetrahydro-1H-3-aza-acenaphthylen-3-yl)-butyl]-carbamic acid tert-butyl esterAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Over a suspension of 7,8-Dimethoxy-2a,3,4,5-tetrahydro-2H-3-aza-acenaphthylen-1-one (0.950 g, 4.1 mmol), K2CO3 (1.89 g, 13.6 mmol) and NaI (0.061 g, 0.4 mmol) in DMF (20 ml) is slowed added (4-Bromo-butyl)-carbamic acid tert-butyl ester (1.09 g, 4.32 mmol) and the mixture is stirred overnight. Then, water (40 ml) and ethyl acetate (40 ml) are added and the layers are separated. The aqueous phase is extracted with ethyl acetate (2×40 ml). The organic layers are collected and washed with water (3×40 ml). After drying with Na2SO4, filtration and vacuum concentration, a brown oil is obtained, which is purified by silicagel chromatography using a gradient of CH2Cl2/methanol (from 100% to 98% CH2Cl2) to obtain a brown solid (0.730 g, 45% yield)

Aufarbeitung

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×40 ml)
  3. customThe organic layers are collected
  4. washwashed with water (3×40 ml)
  5. dry with materialAfter drying with Na2SO4, filtration and vacuum concentration
  6. customa brown oil is obtained
  7. customwhich is purified by silicagel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-10329b214e8c4c7994c7ecb739fde7d7
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553965B2

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