Dimethylformamide → tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

HRID 33199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33199
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17](OS(C(F)(F)F)(=O)=O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([C:27]#[N:28])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 181732813-(tert-butoxycarbonyl)-7-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Produkt 1

HCID 18173275tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-(tert-butyloxycarbonyl)-7-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine (4.78 g, 12.1 mmol), zinc cyanide (1.42 g, 15.6 mmol) and tetrakis-triphenylphosphine palladium (0) (1.4 g, 1.2 mmol, 10 mol %), in dry dimethylformamide (50 ml) was stirred at 100° C. for 3 h under argon. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (120 ml) and filtered. The filtrate was washed with saturated aqueous sodium bicarbonate (100 ml), then water (2×50 ml), then brine (50 ml). The organic layer was dried over sodium sulfate and evaporated in vacuo to give brown oil, which was purified by chromatography on silica gel with 20-100% ethyl acetate—hexane elution to give the title compound (0.765 g, 23%) as a brown oil.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with saturated aqueous sodium bicarbonate (100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give brown oil, which
  6. customwas purified by chromatography on silica gel with 20-100% ethyl acetate—hexane elution

Quellen und Nachweise

ORD-Eintrag
ord-80acd03965e04733a86ece3b6b9d8861
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429579B2

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