Methyl iodide → HCID 21473342, Verbindung

HRID 440248

Reaktionsgleichung

Reaktionsgleichung von HRID 440248
[H-].[Na+].[CH3:3]I.[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]([OH:24])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>O1CCCC1>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH:15]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]([O:24][CH3:3])[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 214733471-t-Butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine

Produkt 1

HCID 21473342HCID 21473342, VerbindungAusbeute 79,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 10 ml of anhydrous tetrahydrofuran was added 0.34 g (0.0085 mole) of a 60% sodium hydride-mineral oil, and while stirring the mixture at 45° to 50° C., 1.21 g (0.0085 mole) of methyl iodide was added thereto. To the mixture was added dropwise a solution of 2.37 g of 1-t-butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine obtained in Reference example 17 (1) dissolved in 10 ml of anhydrous tetrahydrofuran, and the mixture was further stirred at the same temperature for 1 hour. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was supplied to silica gel column chromatography (the eluent used was a mixture of methyl acetate: toluene = 1 : 4) to obtain 1.98 g of 1-t-butoxycarbonyl-3-methoxy-4-phenylaminopyrrolidine as white crystals.

Aufarbeitung

  1. stirringthe mixture was further stirred at the same temperature for 1 hour
  2. customthe solvent was removed under reduced pressure
  3. additiona mixture of methyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-96053ac08ae847158f1522d21ca752eb
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519016

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