1-Undecyn-3-ol → 5-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-one

HRID 977596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977596
Br[C:2]1[N:7]=[C:6]([CH2:8][CH:9]2[O:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1.[CH:15]#[C:16][CH:17]([OH:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(N(CC)CC)C.O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[OH:26][CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16]#[C:15][C:2]1[N:7]=[C:6]([CH2:8][CH:9]2[O:13][C:12](=[O:14])[CH2:11][CH2:10]2)[CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 2

HCID 2477661-Undecyn-3-olHCID 199664915-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one

Produkt 1

HCID 1317190785-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-oneAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 500 mg of 5-[(6-bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one in 13 ml of triethylamine and 2 ml of tetrahydrofuran is mixed with 350 mg of (3RS)-1-undecin-3-ol, 37 mg of bis-(triphenylphosphine)-palladium(II) chloride and 5 mg of copper(I) iodide and the mixture is stirred for 3 days at room temperature. The reaction mixture is evaporated to dryness, distributed between water and ethyl acetate, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/0-35% ethyl acetate. 294 mg of 5-(6-[(3RS)-3-hydroxy-1-undecinyl]-2-pyridyl-methyl}-tetrahydrofuran-2-one is obtained as oil.

Aufarbeitung

  1. customThe reaction mixture is evaporated to dryness
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with hexane/0-35% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c7081e8db41e4b5aa298f80153af9a59
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614634

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