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

HRID 428587

Reaktionsgleichung

Reaktionsgleichung von HRID 428587
[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 8028TetrahydrofuranLösungsmittel2×

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 THF (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 (100mix2). 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 (100mix2)
  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-ea4de7219b4046fd92e2d8cd81bd5517
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313302B2

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