Sodium hydride → 1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione

HRID 53898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53898
[NH:1]1[C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22][N:1]1[C:5]2[C:6](=[O:12])[N:7]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1)([CH3:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 3085877Aldisine

Produkt 1

HCID 110589801,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dioneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 500 mg amount of the 6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione (aldisin) described in the reference (Prager, R. et al: Aust. J. Chem., 43, p. 355-365 (1990)) was added to a 20 ml dimethylformamide suspension of 252 mg of sodium hydride (60% oil). The mixture was stirred at room temperature for 1 hour. A 1.12 ml amount of trimethylsilylethoxymethyl chloride was added under ice cooling, the mixture was stirred at room temperature for 3 hours, then a saturated aqueous solution of ammonium chloride was added and extraction was performed by ethyl acetate. The extract was washed with saturated saline, dried, filtered, and concentrated under reduced pressure to obtain a residue which was purified by silica gel column chromatography (hexane:ether acetate=6:1) to obtain 623 mg of the above-referenced compound (8) (yield 48%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextraction
  3. washThe extract was washed with saturated saline
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas purified by silica gel column chromatography (hexane:ether acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-1c18622ef01b47798c68d59f65e97b4b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621099

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