Triethylamine → 7-[3,5-Difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane

HRID 602003

Reaktionsgleichung

Reaktionsgleichung von HRID 602003
[CH:1]12[NH:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.C(N(CC)CC)C.[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([F:29])[C:24]=1[O:25][CH2:26][C:27]#[CH:28])[C:19](Cl)=[O:20]>C(OCC)(=O)C>[F:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([F:29])[C:24]=1[O:25][CH2:26][C:27]#[CH:28])[C:19]([N:7]1[CH:6]2[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]2)=[O:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5492407-Azabicyclo[4.1.0]heptaneHCID 574456963,5-Difluoro-4-(2-propynyloxy)benzoyl chloride

Produkt 1

HCID 577011787-[3,5-Difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptaneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture of 1.45 g of 7-azabicyclo[4.1.0]heptane, 2 ml of triethylamine and 3 ml of ethyl acetate was added dropwise to a mixture of 10 ml of ethyl acetate and 2.3 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid chloride under ice-cooling. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.8 g of 7-[3,5-difluoro-4-(2-propynyloxy)benzoyl]-7-azabicyclo[4.1.0]heptane represented by the formula:

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a782385e680e44d1999e104da8b8b99f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902400B2

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