Water → (S)-1-benzyl-3-fluoropyrrolidine

HRID 381736

Reaktionsgleichung

Reaktionsgleichung von HRID 381736
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[F-:25].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([F:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86583595(R)-1-Benzyl-3-pyrrolidinol tosylate

Produkt 1

HCID 20694590(S)-1-benzyl-3-fluoropyrrolidineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-1-benzyl-3-pyrrolidinol-tosylate (3.06 g, 9.24 mmol) in THF (30 ml) was added 1.0M solution of tetrabutylammonium fluoride in THY (37.0 ml, 37.0 mmol) at room temperature. After 1.5 h stirring at reflux temperature, water (150 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 ml×2). The combined extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH:50/1) to afford 1.18 g (71%) of brown oil.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give brown oil, which
  8. customwas purified by column chromatography (silica gel: 80 g, CH2Cl2/MeOH:50/1)

Quellen und Nachweise

ORD-Eintrag
ord-78f0107feab344599c53251389ec556c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307061B2

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