Water → rac-(3R,4S)-1-benzylpyrrolidine-3,4-diol

HRID 366886

Reaktionsgleichung

Reaktionsgleichung von HRID 366886
[CH2:1]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:14].[OH2:18]>CC(C)=O>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:18])[CH:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 5615061-Benzyl-2,5-dihydropyrrole

Produkt 1

HCID 536645rac-(3R,4S)-1-benzylpyrrolidine-3,4-diolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To the solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, 15.0 g of water, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at ambient temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio). After completion, acetone was evaporated under reduced pressure, neutralized by NaOH (aq), and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 17.4 g of 1-benzyl-3,4-dihydroxypyrrolidine (yield 90.0%) was obtained and 1-benzyl-3-pyrroline was not recovered.

Aufarbeitung

  1. customto react for 5 days at ambient temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio)
  2. customAfter completion, acetone was evaporated under reduced pressure
  3. extractionextracted with toluene and water
  4. customAfter the solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c9a2c492705a49d9ad78a09a307146c1
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130338

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