1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86705049, Verbindung

HRID 1477885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477885
[CH3:1][S:2]([CH2:5]P(=O)(OCC)OCC)(=[O:4])=[O:3].[Li+].[Cl-].C1CCN2C(=NCCC2)CC1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([N:41]2[C:49]3[C:44](=[C:45]([CH:50]=O)[CH:46]=[CH:47][CH:48]=3)[CH:43]=[CH:42]2)([CH2:39][CH3:40])[C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=1>CC#N.C(Cl)Cl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([N:41]2[C:49]3[C:44](=[C:45](/[CH:50]=[CH:5]/[S:2]([CH3:1])(=[O:3])=[O:4])[CH:46]=[CH:47][CH:48]=3)[CH:43]=[CH:42]2)([CH2:39][CH3:40])[C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=1

Komponenten

7

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 533797Diethyl (methanesulfonylmethyl)phosphonateHCID 86705048HCID 86705048, Verbindung

Produkt 1

HCID 86705049HCID 86705049, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of diethyl methylsulfonylmethylphosphonate (1.05 g, 4.56 mmol) in CH3CN (30 mL) at RT was added LiCl (0.16 g, 3.80 mmol) and DBU (2.40 g, 9.56 mmol). After 5 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate (1.35 g, 3.80 mmol) in CH3CN (10 mL) was added dropwise. The resulting mixture was stirred for 4 hours at RT. Then it was diluted with DCM (50 mL) and the organic layer was washed with water (30 mL), dried over Na2SO4, filtered. After removal of the solvent, the residue was purified via column chromatography (0-30% EtOAc/hexanes) to provide the title compound. LC/MS m/z=432.0[M+H]+.

Aufarbeitung

  1. washthe organic layer was washed with water (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customAfter removal of the solvent
  5. customthe residue was purified via column chromatography (0-30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e3a6d44ae933402899f3c19bf27ba51b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403807B2

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