Sodium Carbonate → 1-(2,4,5-Trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 323342
[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][O:22][C:23]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:24]=1[C:25](Cl)=[O:26].C(OCC)(=O)C.C(O)C>C(OCC)(=O)C.O.C(OCC)(=O)C>[CH3:21][O:22][C:23]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:24]=1[C:25]([N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:26]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 27608092,4,5-Trimethoxybenzoyl chlorideHCID 184645642-(3-Phenylpyrrolidin-3-yl)ethanolHCID 21584252Ethanol ethylacetate

Produkt 1

HCID 184648671-(2,4,5-Trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (1.8 mmol) and sodium carbonate (0.76 g, 7.2 mmol) in ethyl acetate/water (10 mL/10 mL). With stirring, add a solution of 2,4,5-trimethoxybenzoyl chloride (1.1 g, 1.8 mmol) in ethyl acetate (1 mL). After 18 hours, separate the layers and extract the aqueous layer twice with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 9/1 ethyl acetate/ethanol to give the title compound.

Aufarbeitung

  1. customseparate the layers
  2. extractionextract the aqueous layer twice with ethyl acetate
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-aa360c8fa2a5439d806f2f4ba8a49f94
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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