Aniline → 1-t-Butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine

HRID 440246

Reaktionsgleichung

Reaktionsgleichung von HRID 440246
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[O:13][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]([OH:13])[CH2:12]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Produkt 1

HCID 214733471-t-Butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidineAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In 20 ml of ethyl alcohol was dissolved 5 g (0.027 mole) of 1-t-butoxycarbonyl-3-epoxypyrrolidine, and 12.6 g (0.135 mole) of aniline was added thereto. The mixture was refluxed by heating for 20 hours. After the mixture was cooled to room temperature, the solvent was removed under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of ethyl acetate : toluene = 1 : 4) to obtain 4.85 g of 1-t-butoxycarbonyl-3-hydroxy-4-phenylaminopyrrolidine as yellowish brown crystals.

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was refluxed
  3. temperatureby heating for 20 hours
  4. customthe solvent was removed under reduced pressure
  5. additiona mixture of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8aaeeadb30e94af6909ace50f1acf211
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05519016

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