Dimethylformamide → 3-[2-(4-{2-Methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol

HRID 580959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580959
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]([O:6][CH2:7][CH2:8][O:9][CH3:10])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][N:16]([CH3:19])[CH:17]=O>C(N(CC)CC)C.[OH-].[Na+].[Cu]I>[CH3:10][O:9][CH2:8][CH2:7][O:6][C:5]1[C:11]([CH3:13])=[CH:12][C:2]([C:3]#[C:4][C:5]2([OH:6])[CH:11]3[CH2:13][CH2:19][N:16]([CH2:17][CH2:12]3)[CH2:15]2)=[CH:3][C:4]=1[CH3:14]

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 541527811-(4-Bromo-2,6-dimethylphenoxy)-2-methoxyethane

Produkt 1

HCID 678504423-[2-(4-{2-Methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8471TriethylamineLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane (704 mg) and copper (I) iodide (48 mg) in dimethylformamide (DMF) (5.5 ml) and triethylamine (2.7 ml) at ambient temperature and under an atmosphere of argon. The mixture was heated at 65° C. for 14 hours, cooled to ambient temperature, diluted with 2M aqueous sodium hydroxide (20 ml) and extracted with diethyl ether (5×100 ml). The ethereal extracts were combined, washed with water (100 ml) and saturated brine (100 ml), dried (K2CO3) and evaporated. The residue was crystallised from acetonitrile to give 3-[2-(4-{2-methoxyethoxy}-3,5-dimethylphenyl)ethynyl]quinuclidin-3-ol (130 mg) as a solid, m.p. 120° C.; microanaylsis, found: C, 72.4; H, 8.2; N, 4.1%; C2OH27NO3 requires: C, 72.9; H, 8.3; N, 4.2%; NMR([CD3)2SO): 1.3(1H,m), 1.57(1H,m), 1.9(3H,m), 2.21(6H,s), 2.65(4H,m), 2.8(1H,d), 3.02(1H,d), 3.31(3H,s), 3.61(2H,m), 3.87(2H,m), 5.5(1H,br) and 7.07(2H,s); m/z 330 (M+H).

Aufarbeitung

  1. customat ambient temperature
  2. temperaturecooled to ambient temperature
  3. extractionextracted with diethyl ether (5×100 ml)
  4. washwashed with water (100 ml) and saturated brine (100 ml)
  5. dry with materialdried (K2CO3)
  6. customevaporated
  7. customThe residue was crystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-fbe52ca1885e4747bfdcb31e83805588
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919793

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