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Water → 1-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine

HRID 358898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 358898
[H-].[Na+].[CH3:3]I.[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([OH:17])[CH:14]([N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O>O1CCCC1>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([O:17][CH3:3])[CH:14]([N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200671491-t-Butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine

Produkt 1

HCID 200671541-t-Butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidineAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

0.19 g (0.0047 mole) of sodium hydride (as a 60% w/w dispersion in mineral oil) and 0.89 g (0.0063 mole) of methyl iodide were added, in that order, to a solution of 1.2 g (0.0031 mole) of 1-t-butoxycarbonyl-3-dibenzylamino-4-hydroxypyrrolidine [prepared as described in Step (1) above] dissolved in 10 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 5 hours. At the end of this time, water was added to the reaction mixture, which was then extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, eluted with a 5:95 by volume mixture of ethyl acetate and toluene, to give 0.99 g of 1-t-butoxycarbonyl-3-dibenzylamino-4-methoxypyrrolidine as a colorless oil.

Aufarbeitung

  1. extractionwas then extracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with a 5:95 by volume mixture of ethyl acetate and toluene

Quellen und Nachweise

ORD-Eintrag
ord-04f769001bab4f64ade66d45a0e6d28c
Quelldatensatz
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04997943

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