Acetonitrile → HCID 58690204, Verbindung

HRID 2066376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2066376
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[C:17]([NH:24][OH:25])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(#N)C.N12CCCN=C1CCCCC2>O.Cl>[C:20]([O:19][C:17]([NH:24][O:25][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2[C:8](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]1=[O:16])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 93575N-(4-Bromobutyl)phthalimideHCID 97534tert-butyl N-hydroxycarbamate

Produkt 1

HCID 58690204HCID 58690204, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of commercially available N-(4-bromobutyl)phthalimide (2.82 g, 10 mmol) and N-Boc-hydroxylamine (2.08 g, 15.6 mmol) was added acetonitrile (2 ml) and successively 1,8-diazabicyclo[5.4.0]undec-7-ene (2.25 ml, 15 mmol). The reaction mixture was stirred at room temperature for 30 min and then at 50° C. for 2 days. It was diluted with a mixture of water (30 ml) and 1 N hydrochloric acid (20 ml). It was extracted with ethyl acetate (2×100 ml). The organic phase was washed with brine (50 ml) and was dried over magnesium sulphate. The crude product was purified by chromatography on silica (60 g), using a gradient of heptane/ethyl acetate 1:0 to 0:1 as eluent to give 2.08 g of 2-(4-(tert-butoxycarbonylaminoxy)butyl)isoindole-1,3-dione.

Aufarbeitung

  1. waitat 50° C. for 2 days
  2. extractionIt was extracted with ethyl acetate (2×100 ml)
  3. washThe organic phase was washed with brine (50 ml)
  4. dry with materialwas dried over magnesium sulphate
  5. customThe crude product was purified by chromatography on silica (60 g)

Quellen und Nachweise

ORD-Eintrag
ord-35b364ed8c6d4108a015702cb600231b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293708B2

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