Water → (S)-1-Benzyl-3-chloropyrrolidine

HRID 382300

Reaktionsgleichung

Reaktionsgleichung von HRID 382300
[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])(O)=O.[Na+].O.C(Cl)(Cl)(Cl)[Cl:40]>>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([Cl:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 5

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Produkt 1

HCID 53640613(S)-1-Benzyl-3-chloropyrrolidineAusbeute 72 %

Versuchsvorschrift

To a stirred solution of (R)-1-benzyl-3-pyrrolidinol (886 mg, 5.0 mmol) in CCl4 (20 ml) was added triphenylphosphine (1.574 g, 6.0 mmol) at rt. After 20 h stirring at reflux temperature, the solvent was evapolated. Saturated NaHCO3 aqueous solution and water was added to the residue, and the mixture was extracted with AcOEt. The extract was brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1) to give 706 mg (72%) of pale yellow oil.

Aufarbeitung

  1. temperatureat reflux temperature
  2. extractionthe mixture was extracted with AcOEt
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give brown oil, which
  6. customwas purified by column chromatography (silica gel; 100 g, CH2Cl2/MeOH: 50/1-45/1)

Quellen und Nachweise

ORD-Eintrag
ord-05a87c677493455388288396b292a2c3
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310061B2

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