Potassium Carbonate → (2S,4S)-4-fluoro-1-[[N-(5-hydroxypentyloxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

HRID 555700

Reaktionsgleichung

Reaktionsgleichung von HRID 555700
C([C:4]12[CH2:11][CH2:10][C:7]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])([CH2:8][CH2:9]1)[CH2:6][CH2:5]2)(O)=O.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].[C:31](=O)([O-:33])[O-:32].[K+].[K+]>CN(C)C=O>[F:21][C@@H:19]1[CH2:20][N:16]([C:14](=[O:15])[CH2:13][NH:12][C:7]23[CH2:10][CH2:11][CH:4]([CH2:5][CH2:6]2)[CH2:9][CH:8]3[C:31]([O:33][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[O:32])[C@H:17]([C:22]#[N:23])[CH2:18]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1187091-Pentanol, 5-bromo-HCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Produkt 1

HCID 66987785(2S,4S)-4-fluoro-1-[[N-(5-hydroxypentyloxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(2S,4S)-1-[[N-(4-Carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg), 5-bromo-1-pentanol (18.7 μL), potassium carbonate (23.5 mg), and N,N-dimethylformamide (1.5 mL) were mixed together. The mixture was stirred at room temperature for 4 hours. The insoluble materials in the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column (eluant:chloroform:methanol=10:1) to give (2S,4S)-4-fluoro-1-[[N-(5-hydroxypentyloxycarbonylbicyclo[2.2.2]oct-1-yl)amino]acetyl]pyrrolidine-2-carbonitrile (32.4 mg).

Aufarbeitung

  1. filtrationThe insoluble materials in the mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by a silica gel column (eluant:chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-00fe0da65bab43aaa74735d021b73001
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053465B2

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